Saturday, May 31, 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.
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.
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.
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.
The Joe Napoli Duo in the Brown Room
2:00 PM - 6:00 PMHead to the Brown Room for a set by musician Joe Napoli.
Fun on the Lawn
3:00 PM - 4:00 PMThe possibilities are endless! Join us on the Grand Lawn at Congress Hall for a fun mystery activity!
Ray Gervato at the Rusty Nail
5:00 PM - 9:00 PMJoin us at the Rusty Nail for an acoustic set by Ray Gervato. You’ll love his voice and amazing arrangements of some of classic rock tunes.
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.
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!
The Stingers at The Pridwin
7:00 PM - 10:00 PMRelax and enjoy a set of music by local band, The Stingers
Robert Bruey at Baron’s Cove
7:00 PM - 10:00 PMHead to the lounge for a set of music by Robert Bruey!
Smooth Edge in the Boiler Room
9:30 PM - 1:00 AMHead down to the Boiler Room for a high-energy set by band, Smooth Edge.