Just-launched Summer Mondays at Shelter Island’s The Pridwin Make the Weekend Last Longer
There’s something quietly rebellious, and incredibly chic, about choosing to stay when everyone else is leaving. On Shelter Island, The Pridwin Hotel & Cottages has tapped into that feeling with a new tradition that feels both luxurious and laid-back: Summer Mondays.
Set against 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 long weekend.
Monday, Reimagined
Forget the Sunday scaries. At The Pridwin, your week starts with a complimentary cruise aboard the resort’s private boat, Fred’s Folly, a vintage-chic name for a vessel that delivers serious summer magic. Picture a breezy ride across Peconic Bay, cool drink in hand, picnic basket at your feet, as the sky glows in those candy-colored tones only a Shelter Island sunset can produce. Or maybe you’re more of a morning person, scones at sunrise, the water glassy and calm, with the week unfolding gently ahead of you.
Summer Mondays are exactly what they sound like: an invitation to stretch out your weekend and ease into the week in the most meaningful way. All it takes is a Sunday overnight stay between July 13 and September 1, and you’re in. The result? A rhythm that feels slower, more intentional, and thoroughly satisfying.
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 summer.
With 49 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 a 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.
There’s something powerful about reclaiming Monday, about deciding that the week starts not with chaos, but with clarity. With a spa treatment, a second helping of breakfast, a breeze off the bay. That’s what Summer Mondays at The Pridwin offer: a new kind of rhythm, where rest is prioritized, connection is easy, and the weekend doesn’t have to end at checkout.
