Friday, August 1, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive adventure to learn about majestic birds of prey like falcons and hawks.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Crops & Clues
10:00 AM - 11:00 AMExplore Beach Plum Farm on a clue-filled treasure hunt!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Water Games
12:00 PM - 1:00 PMBeat the heat on the Grand Lawn at Congress Hall!
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Don Evans Duo at the Rusty Nail
1:30 PM - 4:30 PMHead over to the Rusty Nail for a set of great blues classics and electric instrumentals from the Don Evans duo.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Shell Hunt & Craft
4:00 PM - 5:00 PMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Camille Peruto at the Rusty Nail
5:00 PM - 9:00 PMHead to the Rusty Nail for a set by musician Camille Peruto.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Kenneth Richardson at the Ebbitt Room
6:00 PM - 10:00 PMEnjoy live music performed by acclaimed pianist Kenneth Richardson every week, Thursday through Sunday nights.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Lis Bockelman at the Brown Room
7:00 PM - 11:00 PMHead over to The Brown Room for a set of music by Lis Bockelman.
Jeff LeBlanc at The Pridwin
7:00 PM - 10:00 PMRelax and enjoy a set of music by local artist, Jeff LeBlanc.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Twisted Livin' in the Boiler Room
9:30 PM - 1:00 AMHead down to The Boiler Room for a set of music by Twisted Livin.'
Saturday, August 2, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Sag Harbor Farmers Market with East End Farmers Markets
9:00 AM - 1:00 PMJust a short drive from Baron's Cove, take a stroll through the weekly Sag Harbor Farmers Market.
Brunch with the Craft Studio at Baron’s Cove
10:00 AM - 12:00 PMBring the family to a Saturday brunch at Baron's, where your little ones will enjoy a fun and engaging craft workshop.
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Beach Volleyball
12:00 PM - 1:00 PMWe're serving up some fun on the beach!
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Max Davey Duo at The Rusty Nail
1:30 PM - 4:30 PMHead to The Rusty Nail for a set by the Max Davey Duo!
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Ray Gervato in the Brown Room
2:00 PM - 6:00 PMJoin us in the Brown Room for an acoustic set by Ray Gervato. You’ll love his voice and amazing arrangements of some of classic rock tunes.
Fun on the Lawn
4:00 PM - 5:00 PMThe possibilities are endless! Join us on the Grand Lawn at Congress Hall for a fun mystery activity!
Dave Kelly at the Rusty Nail
5:00 PM - 9:00 PMHead over to the Rusty Nail for a set of music by Dave Kelly.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Kenneth Richardson at the Ebbitt Room
6:00 PM - 10:00 PMEnjoy live music performed by acclaimed pianist Kenneth Richardson every week, Thursday through Sunday nights.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Darin MacDonald in the Brown Room
7:00 PM - 11:00 PMHead over to The Brown Room for a set of music by Darin MacDonald!
Lawrence Cooley at Baron’s Cove
7:00 PM - 10:00 PMHead to the lounge for a set of music by Lawrence Cooley!
The Stingers at The Pridwin
7:00 PM - 10:00 PMRelax and enjoy a set of music by local band, The Stingers
Yachtzee Trio in the Boiler Room
9:30 PM - 1:00 AMHead down to The Boiler Room for an energetic set of classic rock and roll songs from the 60's all the way to the 2000's.
Sunday, August 3, 2025
Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and $40 buckets all day long!
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch designed to wake up your muscles and boost circulation.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Soccer on the Lawn
10:00 AM - 11:00 AMHead to the Grand Lawn at Congress Hall for a good old-fashioned game of soccer!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Beach Games
12:00 PM - 1:00 PMJoin us on the Congress Hall Beach for some friendly competition.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Chad Morales at the Brown Room
2:00 PM - 6:00 PMHead over to The Brown Room for a set of music by Chad Morales!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Bossa Nova Trio at The Pridwin
4:00 PM - 8:00 PMRelax and enjoy a set of music by local band, the Bossa Nova Trio.
Terry & Dave’s Sing Along at The Rusty Nail
5:00 PM - 9:00 PMHead to the Nail for a little bit of sing-along fun led by a dynamic duo!
Kenneth Richardson at the Ebbitt Room
6:00 PM - 10:00 PMEnjoy live music performed by acclaimed pianist Kenneth Richardson every week, Thursday through Sunday nights.
Chad Morales at the Brown Room
7:00 PM - 11:00 PMHead over to The Brown Room for a set of music by Chad Morales!
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Monday, August 4, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Mahjong Mondays
8:00 AM - 8:00 PMHead to The Nook for a round of Mahjong, the classic game of skill, strategy, and luck.
Sand Art
10:00 AM - 11:00 AMMake your own sand art at the Sandpiper to take home.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Saltwater Sessions at Beach Plum Farm
5:00 PM - 8:00 PMHead to Beach Plum Farm every Monday this summer for a casual celebration of the waters that surround our farm.
Monday Night Carnival at Congress Hall
5:30 PM - 8:30 PMJoin us on the Grand Lawn for Congress Hall's Monday Night Carnival!
Monday Night Movie in the Nook
8:30 PM - 10:00 PMHead down to the Nook for a family-friendly movie selection, complete with cozy bonfires and s'mores!
Tuesday, August 5, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Cape May Diamond Hunting
10:00 AM - 11:00 AMJoin us at Sunset Beach and discover Cape May Diamonds—history washed ashore!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Chefs in Training with Chef Todd
10:00 AM - 11:00 PMKids can cook, too! Join Executive Chef Todd Ruiz at The Pridwin pool’s outdoor kitchen to make a delicious pizza.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Tie Dye Tuesday at the Rusty Nail
1:00 PM - 3:00 PMCreate your own tie dye shirt at the Rusty Nail!
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
National Oyster Day on the Lawn
2:00 PM - 4:00 PMWe're celebrating National Oyster Day the best way we know how—with oysters and perfectly paired Gray Whale Gin cocktails.
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Smokin’ Tuesdays at the Rusty Nail
5:00 PM - 7:00 PMEvery Tuesday, get your groove on to lively music and work up your appetite for a classic pig roast - locally sourced from our farm.
Acoustic Concert Series in The Grove
8:00 PM - 9:00 PMEvery Tuesday night, The Pridwin’s outdoor amphitheater space will light up with live music around the glow of the fire.
Wednesday, August 6, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Art from Nature
10:00 AM - 11:00 AMJoin us at Beach Plum Farm where we will use the nature around us to find inspiration for beautiful pieces of art to take home!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Bingo With Blue
4:30 PM - 6:00 PMJoin Blue the Pig in the Congress Hall Harrison Room for Bingo fun with prizes and surprises!
Wednesday Night BBQs
5:00 PM - 9:00 PMOur beloved Wednesday Night BBQs return this summer! Executive Chef Todd Ruiz has prepared an elevated all-you-can eat cookout menu.
Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Darin has been heard entertaining piano bar audiences around the globe.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Thursday, August 7, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Shell Hunt & Craft
10:00 AM - 11:00 AMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Dive-In-Movie
8:30 PM - 10:30 PMFloat and relax under the stars at our Dive-in-Movie night!
Friday, August 8, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive adventure to learn about majestic birds of prey like falcons and hawks.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Crops & Clues
10:00 AM - 11:00 AMExplore Beach Plum Farm on a clue-filled treasure hunt!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Water Games
12:00 PM - 1:00 PMBeat the heat on the Grand Lawn at Congress Hall!
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Shell Hunt & Craft
4:00 PM - 5:00 PMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Saturday, August 9, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Sag Harbor Farmers Market with East End Farmers Markets
9:00 AM - 1:00 PMJust a short drive from Baron's Cove, take a stroll through the weekly Sag Harbor Farmers Market.
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Beach Volleyball
12:00 PM - 1:00 PMWe're serving up some fun on the beach!
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Fun on the Lawn
4:00 PM - 5:00 PMThe possibilities are endless! Join us on the Grand Lawn at Congress Hall for a fun mystery activity!
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Sunday, August 10, 2025
Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and $40 buckets all day long!
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch designed to wake up your muscles and boost circulation.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Soccer on the Lawn
10:00 AM - 11:00 AMHead to the Grand Lawn at Congress Hall for a good old-fashioned game of soccer!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Beach Games
12:00 PM - 1:00 PMJoin us on the Congress Hall Beach for some friendly competition.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Monday, August 11, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Mahjong Mondays
8:00 AM - 8:00 PMHead to The Nook for a round of Mahjong, the classic game of skill, strategy, and luck.
Sand Art
10:00 AM - 11:00 AMMake your own sand art at the Sandpiper to take home.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Saltwater Sessions at Beach Plum Farm
5:00 PM - 8:00 PMHead to Beach Plum Farm every Monday this summer for a casual celebration of the waters that surround our farm.
Monday Night Carnival at Congress Hall
5:30 PM - 8:30 PMJoin us on the Grand Lawn for Congress Hall's Monday Night Carnival!
Monday Night Movie in the Nook
8:30 PM - 10:00 PMHead down to the Nook for a family-friendly movie selection, complete with cozy bonfires and s'mores!
Tuesday, August 12, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Cape May Diamond Hunting
10:00 AM - 11:00 AMJoin us at Sunset Beach and discover Cape May Diamonds—history washed ashore!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Tie Dye Tuesday at the Rusty Nail
1:00 PM - 3:00 PMCreate your own tie dye shirt at the Rusty Nail!
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Smokin’ Tuesdays at the Rusty Nail
5:00 PM - 7:00 PMEvery Tuesday, get your groove on to lively music and work up your appetite for a classic pig roast - locally sourced from our farm.
Acoustic Concert Series in The Grove
8:00 PM - 9:00 PMEvery Tuesday night, The Pridwin’s outdoor amphitheater space will light up with live music around the glow of the fire.
Wednesday, August 13, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Art from Nature
10:00 AM - 11:00 AMJoin us at Beach Plum Farm where we will use the nature around us to find inspiration for beautiful pieces of art to take home!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Bingo With Blue
4:30 PM - 6:00 PMJoin Blue the Pig in the Congress Hall Harrison Room for Bingo fun with prizes and surprises!
Wednesday Night BBQs
5:00 PM - 9:00 PMOur beloved Wednesday Night BBQs return this summer! Executive Chef Todd Ruiz has prepared an elevated all-you-can eat cookout menu.
Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Darin has been heard entertaining piano bar audiences around the globe.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Thursday, August 14, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Shell Hunt & Craft
10:00 AM - 11:00 AMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Dive-In-Movie
8:30 PM - 10:30 PMFloat and relax under the stars at our Dive-in-Movie night!
Friday, August 15, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive adventure to learn about majestic birds of prey like falcons and hawks.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Crops & Clues
10:00 AM - 11:00 AMExplore Beach Plum Farm on a clue-filled treasure hunt!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Water Games
12:00 PM - 1:00 PMBeat the heat on the Grand Lawn at Congress Hall!
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Shell Hunt & Craft
4:00 PM - 5:00 PMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Saturday, August 16, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Sag Harbor Farmers Market with East End Farmers Markets
9:00 AM - 1:00 PMJust a short drive from Baron's Cove, take a stroll through the weekly Sag Harbor Farmers Market.
Brunch with the Craft Studio at Baron’s Cove
10:00 AM - 12:00 PMBring the family to a Saturday brunch at Baron's, where your little ones will enjoy a fun and engaging craft workshop.
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Beach Volleyball
12:00 PM - 1:00 PMWe're serving up some fun on the beach!
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Fun on the Lawn
4:00 PM - 5:00 PMThe possibilities are endless! Join us on the Grand Lawn at Congress Hall for a fun mystery activity!
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Sunday, August 17, 2025
Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and $40 buckets all day long!
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch designed to wake up your muscles and boost circulation.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Soccer on the Lawn
10:00 AM - 11:00 AMHead to the Grand Lawn at Congress Hall for a good old-fashioned game of soccer!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Beach Games
12:00 PM - 1:00 PMJoin us on the Congress Hall Beach for some friendly competition.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Monday, August 18, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Mahjong Mondays
8:00 AM - 8:00 PMHead to The Nook for a round of Mahjong, the classic game of skill, strategy, and luck.
Sand Art
10:00 AM - 11:00 AMMake your own sand art at the Sandpiper to take home.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Saltwater Sessions at Beach Plum Farm
5:00 PM - 8:00 PMHead to Beach Plum Farm every Monday this summer for a casual celebration of the waters that surround our farm.
Monday Night Carnival at Congress Hall
5:30 PM - 8:30 PMJoin us on the Grand Lawn for Congress Hall's Monday Night Carnival!
Monday Night Movie in the Nook
8:30 PM - 10:00 PMHead down to the Nook for a family-friendly movie selection, complete with cozy bonfires and s'mores!
Tuesday, August 19, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Cape May Diamond Hunting
10:00 AM - 11:00 AMJoin us at Sunset Beach and discover Cape May Diamonds—history washed ashore!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Tie Dye Tuesday at the Rusty Nail
1:00 PM - 3:00 PMCreate your own tie dye shirt at the Rusty Nail!
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Smokin’ Tuesdays at the Rusty Nail
5:00 PM - 7:00 PMEvery Tuesday, get your groove on to lively music and work up your appetite for a classic pig roast - locally sourced from our farm.
Acoustic Concert Series in The Grove
8:00 PM - 9:00 PMEvery Tuesday night, The Pridwin’s outdoor amphitheater space will light up with live music around the glow of the fire.
Wednesday, August 20, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Art from Nature
10:00 AM - 11:00 AMJoin us at Beach Plum Farm where we will use the nature around us to find inspiration for beautiful pieces of art to take home!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Wine Down Wednesday on the Lawn
2:00 PM - 4:00 PMEase into the evening with Wine Down Wednesday on the Grand Lawn.
Bingo With Blue
4:30 PM - 6:00 PMJoin Blue the Pig in the Congress Hall Harrison Room for Bingo fun with prizes and surprises!
Wednesday Night BBQs
5:00 PM - 9:00 PMOur beloved Wednesday Night BBQs return this summer! Executive Chef Todd Ruiz has prepared an elevated all-you-can eat cookout menu.
Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Darin has been heard entertaining piano bar audiences around the globe.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Thursday, August 21, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Shell Hunt & Craft
10:00 AM - 11:00 AMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Summer Harvest Dinner
6:00 PM - 8:00 PMJoin us this August for a Summer Harvest Dinner at The Pridwin Hotel, set on our Front Lawn overlooking the serene waters of Shelter Island.
Dive-In-Movie
8:30 PM - 10:30 PMFloat and relax under the stars at our Dive-in-Movie night!
Friday, August 22, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive adventure to learn about majestic birds of prey like falcons and hawks.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Crops & Clues
10:00 AM - 11:00 AMExplore Beach Plum Farm on a clue-filled treasure hunt!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Water Games
12:00 PM - 1:00 PMBeat the heat on the Grand Lawn at Congress Hall!
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Shell Hunt & Craft
4:00 PM - 5:00 PMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Saturday, August 23, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Sag Harbor Farmers Market with East End Farmers Markets
9:00 AM - 1:00 PMJust a short drive from Baron's Cove, take a stroll through the weekly Sag Harbor Farmers Market.
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Beach Volleyball
12:00 PM - 1:00 PMWe're serving up some fun on the beach!
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Fun on the Lawn
4:00 PM - 5:00 PMThe possibilities are endless! Join us on the Grand Lawn at Congress Hall for a fun mystery activity!
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Sunday, August 24, 2025
Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and $40 buckets all day long!
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch designed to wake up your muscles and boost circulation.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Soccer on the Lawn
10:00 AM - 11:00 AMHead to the Grand Lawn at Congress Hall for a good old-fashioned game of soccer!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Beach Games
12:00 PM - 1:00 PMJoin us on the Congress Hall Beach for some friendly competition.
14th Annual Shelter Island Chamber of Commerce Duck Race
12:00 PM - 1:00 PMThe Chamber of Commerce DUCK RACE is a FUNdraiser in support of the Chamber’s annual community events.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Monday, August 25, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Mahjong Mondays
8:00 AM - 8:00 PMHead to The Nook for a round of Mahjong, the classic game of skill, strategy, and luck.
Sand Art
10:00 AM - 11:00 AMMake your own sand art at the Sandpiper to take home.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Art in the Grove
1:00 PM - 3:00 PMFind inspiration in the Grove, the Pridwin's outdoor amphitheater, and unwind with a little artistic creation.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Saltwater Sessions at Beach Plum Farm
5:00 PM - 8:00 PMHead to Beach Plum Farm every Monday this summer for a casual celebration of the waters that surround our farm.
Monday Night Carnival at Congress Hall
5:30 PM - 8:30 PMJoin us on the Grand Lawn for Congress Hall's Monday Night Carnival!
Monday Night Movie in the Nook
8:30 PM - 10:00 PMHead down to the Nook for a family-friendly movie selection, complete with cozy bonfires and s'mores!
Tuesday, August 26, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Cape May Diamond Hunting
10:00 AM - 11:00 AMJoin us at Sunset Beach and discover Cape May Diamonds—history washed ashore!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Tie Dye Tuesday at the Rusty Nail
1:00 PM - 3:00 PMCreate your own tie dye shirt at the Rusty Nail!
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Smokin’ Tuesdays at the Rusty Nail
5:00 PM - 7:00 PMEvery Tuesday, get your groove on to lively music and work up your appetite for a classic pig roast - locally sourced from our farm.
Acoustic Concert Series in The Grove
8:00 PM - 9:00 PMEvery Tuesday night, The Pridwin’s outdoor amphitheater space will light up with live music around the glow of the fire.
Wednesday, August 27, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at the Sandpiper
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Art from Nature
10:00 AM - 11:00 AMJoin us at Beach Plum Farm where we will use the nature around us to find inspiration for beautiful pieces of art to take home!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea of bubbles on the Grand Lawn at Congress Hall.
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Bingo With Blue
4:30 PM - 6:00 PMJoin Blue the Pig in the Congress Hall Harrison Room for Bingo fun with prizes and surprises!
Wednesday Night BBQs
5:00 PM - 9:00 PMOur beloved Wednesday Night BBQs return this summer! Executive Chef Todd Ruiz has prepared an elevated all-you-can eat cookout menu.
Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Darin has been heard entertaining piano bar audiences around the globe.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Thursday, August 28, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Aqua Aerobics at Beach Plum Farm
10:00 AM - 11:00 AMStart your morning off right with a low impact aerobics class in our pool.
Kids’ Crafts on the Lawn
10:00 AM - 11:00 AMJoin us for Kids’ Crafts on the Grand Lawn at Congress Hall!
Shell Hunt & Craft
10:00 AM - 11:00 AMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Hula Hoops on the Lawn
12:00 PM - 1:00 PMGet outside and enjoy the ultimate throwback activity!
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Oysters & Bubbles
4:00 PM - 6:00 PMA combination as beautiful as the Crescent Beach sunset! Join us for a sips of bubbly and freshly-shucked oysters.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Dive-In-Movie
8:30 PM - 10:30 PMFloat and relax under the stars at our Dive-in-Movie night!
Friday, August 29, 2025
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtaking views of the bay.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive adventure to learn about majestic birds of prey like falcons and hawks.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Crops & Clues
10:00 AM - 11:00 AMExplore Beach Plum Farm on a clue-filled treasure hunt!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Water Games
12:00 PM - 1:00 PMBeat the heat on the Grand Lawn at Congress Hall!
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Shell Hunt & Craft
4:00 PM - 5:00 PMJoin us on an adventure to gather shells, and choose your favorite to turn into a treasured keepsake.
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!
Saturday, August 30, 2025
Rise with the Sun Yoga
6:00 AM - 7:00 AMStart your day by connecting to the rising sun and harnessing its energy to awaken and invigorate the body.
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of complimentary guest bicycles are available on a first-come, first-serve basis.
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing of things on our court.
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and start a game of friendly competition—set before a gorgeous waterfront background.
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the charm of this timeless lawn game meets stunning waterfront views.
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peaceful and rewarding experience for anglers of all skill levels.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Sag Harbor Farmers Market with East End Farmers Markets
9:00 AM - 1:00 PMJust a short drive from Baron's Cove, take a stroll through the weekly Sag Harbor Farmers Market.
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, with views that offer a completely unique perspective of this beautiful destination.
Labor Day Sandcastle Building Contest
10:00 AM - 12:00 PMJoin us on the Congress Hall Beach and wrap up the summer with some friendly competition!
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Culinary Gardening
1:00 PM - 2:00 PMJoin us for a hands-on experience where you'll learn to grow your own fresh herbs and vegetables.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Fun on the Lawn
4:00 PM - 5:00 PMThe possibilities are endless! Join us on the Grand Lawn at Congress Hall for a fun mystery activity!
Blue’s Clubhouse
5:00 PM - 9:00 PMKids aged 5-12 will love Blue's Clubhouse, our structured kids' club that's chock-full of awesome activities and games.
Summer Harvest Dinners at Beach Plum Farm
6:00 PM - 8:00 PMCelebrate the flavors of summer with our Farm-to-Table Dinners, where each meal is a delicious tribute to the season’s freshest bounty.
Sunday, August 31, 2025
Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and $40 buckets all day long!
Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a workout fit for all levels!
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with guided routines for all levels.
Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch designed to wake up your muscles and boost circulation.
Gentle Stretch Class
9:00 AM - 9:50 AMIntegrating yoga movements and gentle stretching, this class warms the muscles and joints, stimulates balance and sets one up for the day.
Soccer on the Lawn
10:00 AM - 11:00 AMHead to the Grand Lawn at Congress Hall for a good old-fashioned game of soccer!
Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! The eggs they lay are a key ingredient in The Pridwin’s culinary creations.
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our sun-kissed backfields.
Beach Games
12:00 PM - 1:00 PMJoin us on the Congress Hall Beach for some friendly competition.
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through this grand hotel's storied past.
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall Pool!
Evening Wind Down Yoga
7:30 PM - 8:30 PMStretch with the tides and exhale your day with a practice on the beach at sunset!