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 ...
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Garden & The Chef
11:00 AM - 12:30 PMJoin our Beach Plum Farm Chef for a guided culinary walk ...
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DJ Tony Steff at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Tony Steff will play jams tha...
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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...
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Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Dar...
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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 ...
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Tunnel Work & Lunch
10:30 AM - 12:30 PMJoin us in the high tunnels at Beach Plum Farm for a hand...
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Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
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DJ Chelsea Lee at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Chelsea will play jams that k...
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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...
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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...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
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Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
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Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
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Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
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Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
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Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
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Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive ...
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Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
Read More
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through...
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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!
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Don Evans at the Rusty Nail
5:00 PM - 9:00 PMHead over to The Rusty Nail for a set of great blues clas...
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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...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
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Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
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Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
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Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
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Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
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Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
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Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
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Memorial Day Sandcastle Building Contest
10:00 AM - 12:00 PMJoin us on the Congress Hall Beach and kick off the summe...
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Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
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Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through...
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Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea ...
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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...
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Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
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Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall P...
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Charlie Wigo at The Rusty Nail
5:00 PM - 9:00 PMCharlie Wigo is the front man of Dead Reckoning, a beachs...
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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...
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Sunday, May 25, 2025
Surfside Sunday
Stop by the Nail this Sunday for $2 off Surfside cans and...
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Beach Bootcamp with Donna Valentine
7:00 AM - 8:00 AMJoin Donna Valentine on the Congress Hall Beach for a wor...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
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Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
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Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
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Rise and Revive: Dynamic Movement Stretch Class
8:00 AM - 9:00 AMStart your day with an energizing full-body stretch desig...
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Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
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Chicken Class with Chef Todd
10:00 AM - 11:00 PMInteract with our friendly flock and offer them a snack! ...
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Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
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Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
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Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through...
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Hang Loose at the Rusty Nail
1:30 PM - 4:30 PMHead down to the Rusty Nail for a high-energy set by band...
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Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
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Treasure Dive
4:00 PM - 5:00 PMStrap on your goggles and splash into the Congress Hall P...
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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...
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Hula Hoops on the Lawn
6:00 PM - 7:00 PMGet outside and enjoy the ultimate throwback activity!
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Dive-In-Movie
8:00 PM - 10:00 PMFloat and relax under the stars at our Dive-in-Movie night!
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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...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
Read More
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
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Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
Read More
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
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Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtakin...
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Kids’ Crafts at Congress Hall
10:00 AM - 11:00 AMJoin us for Kids' Crafts at Congress Hall.
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Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through...
Read More
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea ...
Read More
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.
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Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
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Memorial Day BBQ
5:00 PM - 9:00 PMJoin us this Memorial Day Monday at The Pridwin Hotel on ...
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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...
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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...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
Read More
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
Read More
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
Read More
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
Read More
Strawberry Picking at Beach Plum Farm
9:00 AM - 10:00 AMAs the warm weather ushers in strawberry season, join us ...
Read More
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
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.
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Smokin’ Tuesdays at the Rusty Nail
5:00 PM - 7:00 PMEvery Tuesday, get your groove on to lively music and wor...
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Greg Jones at The Rusty Nail
5:00 PM - 9:00 PMHead to The Rusty Nail for a set of music by Greg Jones!
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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...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
Read More
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
Read More
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
Read More
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
Read More
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtakin...
Read More
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
Read More
Garden & The Chef
11:00 AM - 12:30 PMJoin our Beach Plum Farm Chef for a guided culinary walk ...
Read More
DJ Tony Steff at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Tony Steff will play jams tha...
Read More
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...
Read More
Darin MacDonald at the Brown Room
6:00 PM - 10:00 PMWith exceptional vocals and captivating piano skills, Dar...
Read More
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...
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Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
Read More
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
Read More
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
Read More
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
Read More
Strawberry Picking at Beach Plum Farm
9:00 AM - 10:00 AMAs the warm weather ushers in strawberry season, join us ...
Read More
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
Tunnel Work & Lunch
10:30 AM - 12:30 PMJoin us in the high tunnels at Beach Plum Farm for a hand...
Read More
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
Read More
DJ Chelsea Lee at the Rusty Nail
1:30 PM - 4:30 PMFeaturing a vibrant mix, DJ Chelsea will play jams that k...
Read More
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...
Read More
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...
Read More
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
Read More
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
Read More
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
Read More
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
Read More
Yoga on the Lawn
8:00 AM - 8:00 PMFind balance and serenity while surrounded by breathtakin...
Read More
Falconry at the Farm
10:00 AM - 11:30 PMJoin us at Beach Plum Farm for a thrilling and immersive ...
Read More
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
Read More
Congress Hall History Tour
1:30 PM - 2:30 PMOn a Congress Hall History Tour, you'll be guided through...
Read More
Charlie Wigo Duo at The Rusty Nail
1:30 PM - 4:30 PMHead to The Nail for the Dead Reckoning Duo, led by Charl...
Read More
Camille Peruto at the Rusty Nail
5:00 PM - 9:00 PMHead to the Rusty Nail for a set by musician Camille Peruto.
Read More
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...
Read More
Guest Bicycles
7:00 AM - 8:00 PMExplore Shelter Island by bike! The Pridwin’s fleet of co...
Read More
Tennis & Pickleball
7:00 AM - 8:00 PMPractice your backhand or simply get back into the swing ...
Read More
Beach Yoga
8:00 AM - 9:00 AMJoin us on the Congress Hall Beach and find balance with ...
Read More
Cornhole
8:00 AM - 8:00 PMA Pridwin favorite! Choose a side, pick up a bag, and sta...
Read More
Croquet
8:00 AM - 8:00 PMEnjoy a classic game of croquet at The Pridwin, where the...
Read More
Fishing
8:00 AM - 8:00 PMFishing off the dock at The Pridwin Hotel offers a peacef...
Read More
Kids’ Crafts at Congress Hall
10:00 AM - 11:00 AMJoin us for Kids' Crafts at Congress Hall.
Read More
Kayaks & Paddle Boards
10:00 AM - 8:00 PMExplore Shelter Island’s expansive waterways with ease, w...
Read More
Guided Beach Plum Farm Walking Tour
11:00 AM - 12:00 PMJoin us at Beach Plum Farm and take a stroll through our ...
Read More
Congress Hall History Tour
11:00 AM - 12:00 PMOn a Congress Hall History Tour, you'll be guided through...
Read More
Bubbles on the Lawn
12:00 PM - 1:00 PMGet ready to pop, chase and laugh your way through a sea ...
Read More
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...
Read More
Pool Games
2:00 PM - 3:00 PMJump into excitement at Congress Hall’s pool!
Read More
Ray Gervato at the Rusty Nail
5:00 PM - 9:00 PMJoin us at the Rusty Nail for an acoustic set by Ray Gerv...
Read More
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...
Read More