Family Travel

Tapping Into Shelter Island-Style Nostalgia

by Jeralyn Gerba
All photos courtesy of The Pridwin unless otherwise noted.

A nearly century-old inn with a 21st-century renovation delivers whimsy on the waterfront.

SHELTER ISLAND, New York - Shelter Island sits in between the two forks of Long Island and — physically, spiritually, stylistically — feels like a true blend of the North Fork and the Hamptons. Woodsy up to its waterfront, the island has been an upscale but low-key destination for some time. Even before it was inhabited by white people in the seventeenth century, the island called Manhansack-aha-quash-awamock (“an island sheltered by islands") was a peaceful respite for the Manhasset tribe — and home to the main chief of the Long Island tribes. According to the Shelter Island Historical Society, ferry service began over a century later, when demand for summer retreats soared, thanks to a large contingent of revelers from Brooklyn and Manhattan.

The Pridwin resort has been around since 1927 and has been managed by the Petry family since 1961; 2023 is its first full summer season as part of Cape Resorts, a NY-NJ hospitality company that loves adaptive reuse and historic preservation. The team renovated the 33-room Main House and added two additional freestanding cottages (for 16 total) that stretch across a sloping patch of land facing Crescent Beach. Tennis courts and a very active chicken coop are located up behind the cottages, as is a nice little clearing in the forest with a wooden platform and risers — perfect for some kind of ceremony or nature talk. The cottages are perched up high; a set of stairs leads down to a pretty pool overlooking the water.

A front lawn perfect for cartwheels.
Have your coffee clutch or board game battle here.
Twinning at the game table. Photo by Jeralyn Gerba.
Prime seats in front of a roaring fire.
A simple and fresh outfit for the room.
Everything you need for an overnight in the cottage.
A quiet spot for a gentle rock.

Breakfast, lunch, and dinner are served on the Terrace, an indoor-outdoor space with a double-sided fireplace. The whimsical Crescent Bar is a spacious sitting area ready for whatever fun event is about to unfold, probably with live music. The whole place has a Wes Anderson-approved exaggerated color palette (like lilac and sage green chair cushions). A lower lobby with a game room, gift shop, and mini spa opens onto a front lawn with fire pits. The second floor parlor is a prime spot on a  rainy day with its fireplace, library, and plethora of board games. All around, knickknacks like antique model ships mix with classic New England furnishings like painted Adirondack chairs. A pristine American flag flaps in the wind out front, and just beyond that is a fantastic osprey nest – the great bird likely circling slowly above it.

Rooms and cottages are simple, fresh, and clean, with great light. My family of five took over the largest cottage, a cute two-bedroom and two-bath on two floors, with a kitchenette, living room, and balcony serving a sunny slice of bay views.

Nearly a century’s worth of summer vacations played out on this piece of land, and inveterate residents were watching with bated breath during the handover and refresh — pressure was high to do things right. The aim is romanticized nostalgia — and they nail it. All the various gathering spaces are warm and welcoming. The spaces feel fresh but not precious and just a little worn in, like an Ivy-style button down. Even with kids, we found it easy to hang on property for a weekend without feeling bored or hemmed in. There are complimentary bicycles to explore the island, and the dock across the street makes for easy access to boat rentals and fishing charters. We enjoyed keeping it simple: visiting the chickens, playing corn hole, learning pickleball, collecting shells on the beach, and mastering card games while snacking on fritto misto and burgers.

My kids doing cartwheels on the lawn at sunset reminded me of my childhood summers on the East End. Same salty air, scent of bug spray, sticky s'more fingers, pink sunset — just as The Pridwin intended.

Feeling good! Photo by Jeralyn Gerba.
The tidiest shed that you ever did see. Photo by Jeralyn Gerba.
Kicking camp nostalgia into gear.
A perky little bar setup.
Blue sky on blue bay on blue pool.
Quintessential East Coast summer scene.
Local icon.

Book It

Click here for reservations.

Get There

Two ferries, one at each end of the island, operate on a loop daily. The North Ferry departs from the North Fork of Long Island and the South Ferry from Sag Harbor. Cars, people, and bicycles can ride the ferry without a reservation; payment is made on board. The boat ride is ten minutes over the Shelter Island Sound.

To get to the ferry from the North Fork, you can drive or book a seat on the Hampton Jitney to the North Ferry terminal in Greenport and then walk aboard. If you take the Long Island Railroad to the Greenport Train Station and text The Pridwin (+1-631-888-9421) for the ride, they'll pick you up (free of charge) in their boat, Fred's Folly, and take you to the hotel dock. Classy! If you have the money but not the time, Tailwind Air offers a 45-minute seaplane flight from 23rd Street in Manhattan to the sparkling waters of Crescent Bay, right in front of the hotel.

Spend More Time on the East End

See Fathom's Guide to the Hamptons

We make every effort to ensure the information in our articles is accurate at the time of publication. But the world moves fast, and even we double-check important details before hitting the road.