above: (left) The Pridwin Hotel & Cottages captures the nostalgic charm of Shelter Island’s shoreline—where fall foliage meets timeless coastal elegance. (center) At The Pridwin, even a quiet moment becomes an occasion—effervescent flutes of champagne served with a side of old-world glamour. (right) A warm welcome steeped in nostalgia: The Pridwin’s check-in desk pairs maritime charm with vintage flair, setting the tone for a timeless seaside say.
Photographs: Provided by The Pridwin
Luxurious and laid-back, The Pridwin Hotel & Cottages is the new in-the-grid destination with off-the-grid relaxation. Fall weekends feature curated programming like culinary/tastings, wine tastings, oyster pop-ups, and fishing charters, as well family-friendly activities such as pumpkin painting and cornhole tournaments. The Sunday Supper Series, a relaxed, chef-driven dining experience, is also a highlight.
Set among ten acres of leafy waterfront and dotted with charming white cottages, The Pridwin has been a treasured escape since 1927. It’s the kind of place that honors tradition while offering just enough refresh to keep it current, thanks to its thoughtful revamp by Cape Resorts. And now, it’s redefining the art of the fall weekend.
A SEAMLESS JOURNEY TO ESCAPE
Getting there is delightfully uncomplicated. With daily Jitney and LIRR service to Greenport, the journey from city stress to island serenity happens in a matter of hours. And upon arrival, The Pridwin whisks guests from Greenport Harbor via private boat straight to the resort dock, a detail that feels James Bond-esque. The moment you step onto the lawn, a slower, more sensory vibe kicks in.
FALL, CURATED
Each day at The Pridwin has the feel of a lovingly curated itinerary from a well-traveled friend. Morning yoga on the lawn flows into island-inspired treatments at the Pridwin Spa. Afternoons might include paddleboarding, kayaking or dockside fishing, or something more land-bound like pickleball, croquet or a bike ride through the nearby Mashomack Preserve. The property offers enough to keep you entertained without overwhelming your senses. There’s a rhythm here: activity and stillness, sunshine and shade, connection and quiet. And yes, there’s a Mahjong Monday in the Nook, should the mood strike. Evenings are pure East End magic.
“Oysters and Bubbly” at The Terrace happens just as the sky starts to blush. Wednesday night barbecues on the lawn are anchored by live music and capped with fireside s’mores by the bay. There are culinary gardening workshops to bring home a bit of edible wisdom, and Movie Night in the Grove, where you can lie back under the stars and remember what it felt like to be a kid in late fall.
CLASSIC CHARM MEETS CONTEMPORARY EASE
With 33 guest rooms and 16 private cottages, The Pridwin manages to feel both intimate and expansive. Interiors lean into nostalgic Americana with white clapboard, striped awnings and curated art, while offering modern comforts that make staying a breeze, whether you’re working remotely (laptop in one hand, crisp drink in the other) or unplugging entirely.
Dining is another highlight. Executive Chef Todd Ruiz brings a farm-and-sea-to-table approach to the menu at The Terrace, where the views of the bay are almost as memorable as the food itself. Think seasonal, locally sourced dishes served just steps from the water.
The Pridwin offers a new kind of rhythm, where rest is prioritized, connection is easy, and the weekend doesn’t have to end at checkout.
So linger. Stay a little longer. Monday will thank you.
To book your visit, visit: caperesorts.com
FALL FEST
The Pridwin hosts a Fall Fest weekend in October, featuring classic fall activities including pumpkin painting, sack races, live music, and treats like s’mores and hot cider.
Sunday Supper Series
Enjoy a relaxed, open-air dining experience with a rotating menu of seasonal dishes served family-style.
Weekend Activities
Every fall weekend includes complimentary events like culinary and wine tastings, oyster pop-ups, and fishing charters.
Family Fun
Activities like pumpkin painting, cornhole tournaments, and a bouncy castle are available for families.
Scenic Views and Activities
The hotel’s location on Crescent Beach provides beautiful views and opportunities for kayaking, paddle boarding, pickleball,
and more.
Cozy Atmosphere
The Pridwin offers a cozy and relaxing atmosphere, with nautical touches in the rooms and cottages, and fireplaces for chilly evenings.