
Wednesday, May 21, 2025

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Garden & The Chef
11:00 AM - 12:30 PMJoin our Beach Plum Farm Chef for a guided culinary walk ...

DJ Tony Steff at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Tony Steff will play jams tha...

What’d He Say? at The Rusty Nail
5:00 PM - 9:00 PMHead to The Rusty Nail for an energetic set of local Cape...

Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Dar...
Thursday, May 22, 2025

Strawberry Picking at Beach Plum Farm
9:00 AM - 10:00 AMAs the warm weather ushers in strawberry season, join us ...

Tunnel Work & Lunch
10:30 AM - 12:30 PMJoin us in the high tunnels at Beach Plum Farm for a hand...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

DJ Chelsea Lee at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Chelsea will play jams that k...

The Honeyhawks at the Rusty Nail
5:00 PM - 9:00 PMHead down to the Rusty Nail for a lively set by the The H...
Friday, May 23, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive ...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through...

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!

Don Evans at the Rusty Nail
5:00 PM - 9:00 PMHead over to The Rusty Nail for a set of great blues clas...
Saturday, May 24, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Memorial Day Sandcastle Building Contest
10:00 AM - 12:00 PMJoin us on the Congress Hall Beach and kick off the summe...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through...

Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea ...

Dave Kelly at the Rusty Nail
1:30 PM - 4:30 PMHead over to the Rusty Nail for a set of music by Dave Ke...

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 P...

Charlie Wigo at The Rusty Nail
5:00 PM - 9:00 PMCharlie Wigo is the front man of Dead Reckoning, a beachs...

Darin MacDonald at the Brown Room
7:00 PM - 11:00 PMHead over to The Brown Room for a set of music by Darin M...
Sunday, May 25, 2025

Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and...

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch desig...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! ...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through...

Hang Loose at the Rusty Nail
1:30 PM - 4:30 PMHead down to the Rusty Nail for a high-energy set by band...

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 P...

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 b...

Hula Hoops on the Lawn
6:00 PM - 7:00 PMGet outside and enjoy the ultimate throwback activity!

Dive-In-Movie
8:00 PM - 10:00 PMFloat and relax under the stars at our Dive-in-Movie night!
Monday, May 26, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtakin...

Kids’ Crafts at Congress Hall
10:00 AM - 11:00 AMJoin us for Kids' Crafts at Congress Hall.

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through...

Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea ...

DJ Mike Dempsey at the Rusty Nail
1:30 PM - 4:30 PMHead to the Nail for a set of music by DJ Mike Dempsey.

Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!

Memorial Day BBQ
5:00 PM - 9:00 PMJoin us this Memorial Day Monday at The Pridwin Hotel on ...

Matt DiVenti at the Rusty Nail
5:00 PM - 9:00 PMHead over to The Rusty Nail for a set of music by Matt Di...
Tuesday, May 27, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Strawberry Picking at Beach Plum Farm
9:00 AM - 10:00 AMAs the warm weather ushers in strawberry season, join us ...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

DJ Torey Whom at the Rusty Nail
1:30 PM - 4:30 PMHead to the Nail for a set of music by DJ Torey Whom.

Smokin’ Tuesdays at the Rusty Nail
5:00 PM - 7:00 PMEvery Tuesday, get your groove on to lively music and wor...

Greg Jones at The Rusty Nail
5:00 PM - 9:00 PMHead to The Rusty Nail for a set of music by Greg Jones!
Wednesday, May 28, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtakin...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Garden & The Chef
11:00 AM - 12:30 PMJoin our Beach Plum Farm Chef for a guided culinary walk ...

DJ Tony Steff at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Tony Steff will play jams tha...

What’d He Say? at The Rusty Nail
5:00 PM - 9:00 PMHead to The Rusty Nail for an energetic set of local Cape...

Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Dar...
Thursday, May 29, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Strawberry Picking at Beach Plum Farm
9:00 AM - 10:00 AMAs the warm weather ushers in strawberry season, join us ...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Tunnel Work & Lunch
10:30 AM - 12:30 PMJoin us in the high tunnels at Beach Plum Farm for a hand...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

DJ Chelsea Lee at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Chelsea will play jams that k...

The Honeyhawks at the Rusty Nail
5:00 PM - 9:00 PMHead down to the Rusty Nail for a lively set by the The H...
Friday, May 30, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtakin...

Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive ...

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through...

Charlie Wigo Duo at The Rusty Nail
1:30 PM - 4:30 PMHead to The Nail for the Dead Reckoning Duo, led by Charl...

Camille Peruto at the Rusty Nail
5:00 PM - 9:00 PMHead to the Rusty Nail for a set by musician Camille Peruto.
Saturday, May 31, 2025

Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...

Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...

Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...

Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...

Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...

Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...

Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...

Kids’ Crafts at Congress Hall
10:00 AM - 11:00 AMJoin us for Kids' Crafts at Congress Hall.

Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...

Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...

Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through...

Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea ...

Don Evans Duo at the Rusty Nail
1:30 PM - 4:30 PMHead over to the Rusty Nail for a set of great blues clas...

Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!

Ray Gervato at the Rusty Nail
5:00 PM - 9:00 PMJoin us at the Rusty Nail for an acoustic set by Ray Gerv...

Darin MacDonald at the Brown Room
7:00 PM - 11:00 PMHead over to The Brown Room for a set of music by Darin M...