The trip to Shelter Island starts on the ferry. Whether you arrive from the North Fork or drive on at Sag Harbor, the brief breezy ride signals a reset. With traffic in the rear view and a new coastline ahead, your body starts to relax. That’s the real beginning. And as you wind along the island’s quiet roads and Crescent Beach comes into view, so does The Pridwin, perched like a postcard from the past.
The storied hotel looks like it hasn’t changed since its 1927 opening, a credit to its careful restoration and extensive renovation in 2023. The Cape Resorts design team, led by Colleen Bashaw, knew the importance of preserving the spirit of the original resort, one that hosted families for nearly a century. Now, the refreshed white clapboard exterior is dotted with windows framed in the property’s signature green, the perfect shade to complement its iconic lawn. Inside, original signage and vintage photographs remind guests of the building’s past, in spaces that have been lovingly brought into the present. Coastal ease meets retro camp in a bold new look that trades minimalism for personality: there’s wicker and wood, but also vibrant prints, rich color and collected decor that give it a storybook feel. If Wes Anderson were designing a seaside escape, it might look something like this.
Beyond the 33 rooms in the main building, 16 cottages offer privacy and additional space to unwind, ideal for families, friend groups or anyone who wants to feel like they have a slice of the island to themselves. Many have private decks and there’s just enough distance to make it feel like you’re staying at your own hideaway, while still being a short stroll from dinner or the dock.
The Pridwin is perfectly designed for doing nothing—reading in an Adirondack chair, sipping frosé by the pool or visiting the full-service spa, setup in a cottage among the trees. But if you’re the type who needs just a bit more activity, there’s no shortage of things to do. You can paddleboard or kayak, then try your luck at pickleball, croquet or tennis. Want to venture off-property? Borrow a bike or rent their Moke and cruise around the island or head into Mashomack Preserve for a hike. The kids have their own lineup: a seasonal sailing program, scavenger hunts, crafts and supervised movie nights, which free you up for adult cocktails under the red and pink scalloped awning at The Crescent Bar.
Dining at The Terrace, The Pridwin’s waterfront restaurant, is as much about the setting as it is the food. Watch the sailboats drift past at golden hour as you enjoy plates from a menu that highlights the seasonal bounty: fresh local seafood, garden-picked produce, homemade pasta.
And if you’re able, schedule your visit around a Wednesday. That’s when BBQ Night takes over the lawn, and suddenly you’re in a Norman Rockwell painting with a Negroni in hand. Hotel guests and island regulars grab seats at red-and-white–checked tables, piling plates with elevated cookout fare. There’s a live band. Kids run barefoot. And from your front row seat overlooking Peconic Bay, you’ll understand exactly why people return year after year, summer after summer.
81 Shore Road
Shelter Island, NY 11964-2009
caperesorts.com/pridwin