Discover a serene, cozy side of the Hamptons. From quiet beaches and scenic drives to warming fireside moments, winter offers reflection, adventure, and indulgence. We like to think of Canoe Place Inn as your cozy home base—offering luxury accommodations, waterfront views, and thoughtfully curated experiences for every traveler, in every season.
Winter Beach Walks
Even if swimming is off the table, winter beach walks reveal quiet, meditative beauty. From Ponquogue Beach and Cooper’s Beach to the cliffs at Ditch Plains Beach, the ocean is strikingly serene in the colder months. Fewer visitors mean more privacy—perfect for reflection or for your pup to stretch and play. For a cozy option, grab a bacon, egg & cheese and coffee from Good Ground Tavern, then drive to The Inlet across from Oakland’s Restaurant to enjoy the views from your car.
Wellness & Self-Care Escapes
Slow down and focus on yourself. At our spa (in partnership with SommetBeauty), enjoy massages, facials, and seasonal treatments. Curated wellness experiences—lymphatic treatments, acupuncture, chiropractic care, and infrared sauna sessions with Wave Wellness—provide restorative calm. Sunrise walks along the canal or quiet moments by the fireplace complete the experience
Local favorites also include Doza Yoga in Westhampton Beach, Tremble Pilates in Southampton, and Sculpted by Emily in Hampton Bays.
Winter Outdoor Adventures
Ice skating rinks in East Hampton and Southampton offer festive fun—Southampton’s rink features igloos, games for kids, and Local Burger for a warm bite. Nature preserves like Quogue Wildlife Preserve and Agawam Park provide peaceful walks for families and pets. Crisp air, open space, and quiet trails make winter outdoor adventures refreshing and unhurried.
Arts, Culture & Local Happenings
Explore the Hamptons’ arts scene without the summer crowds. Guild Hall, The Parrish Art Museum, and The Drawing Room showcase contemporary and classic works. For a contemplative escape, LongHouse Reserve offers stunning gardens and art installations. The Church in Sag Harbor hosts exhibitions, live performances, and cultural events in a beautifully restored historic space.
Shopping & Village Strolls
Wander charming villages at a relaxed pace. East Hampton Village and Southampton’s Main Street feature boutiques, galleries, and specialty shops. On the North Fork, Greenport Village offers waterfront views, historic streets, artisanal shops, and cozy cafés—a perfect winter stop for gifts or a warm drink while strolling.
Scenic Drives
Take a scenic winter drive through the Hamptons, where quiet roads lead to charming stops and small indulgences. Pause at Tate’s Bake Shop in Southampton for their signature thin, crispy chocolate chip cookies, baked fresh and perfect for the road, or swing by Grindstone Coffee & Donuts in Sag Harbor for coffee and brioche donuts. Fewer crowds make it easy to explore and discover the Hamptons at a relaxed pace.
Sip, Savor & Taste the East End
On the South Fork, some of our favorite spots include Good Ground Tavern in Hampton Bays, where seasonal American dishes highlight local ingredients; Nick & Toni’s in East Hampton, known for Italian-inspired fare; and Bell & Anchor in Sag Harbor for seafood-focused New American cuisine. Sen offers thoughtfully prepared sushi in a relaxed village setting, while Bistro Eté in Water Mill and Elaia Estiatorio in Bridgehampton bring French and Mediterranean flavors to the table. 1770 House in East Hampton and Fauna in Westhampton Beach round out our picks with approachable, flavorful dishes that make winter dining a pleasure.
On the North Fork, local favorites include Frisky Oyster in Greenport, offering imaginative, seasonal cuisine; Little Creek Oysters for fresh oysters and a relaxed Peconic Bay experience; North Fork Table & Inn in Southold, serving refined American fare in a charming countryside setting; and First & South in Greenport, with creative dishes and a welcoming atmosphere.
Wineries & Vineyards
On the South Fork, Wölffer Estate Vineyard in Sagaponack offers intimate tastings and their seasonal Friday Night Candle Series with live music in a cozy, candlelit setting. Nearby, Channing Daughters Winery in Bridgehampton provides a welcoming tasting room perfect for savoring seasonal varietals.
On the North Fork, many charming vineyards offer unique character and seasonal experiences. North Fork Sites, Bites & Flights allows guests to explore farms, artisanal producers, and wineries, with itineraries tailored by the Canoe Place Inn concierge to match individual tastes.
Craft Beverages
Kidd Squidd in Sag Harbor offers a community-focused craft brewery experience with rotating beers on tap, live music, and engaging local events. Montauk Brewing Company in Montauk serves approachable, well-crafted beers in a laid-back coastal setting. Sagaponack Distillery in Sagaponack crafts estate-grown spirits with a “seed-to-glass” philosophy; guests can enjoy flights and creative craft cocktails in a restored farm structure.
In Greenport Village, Greenport Harbor Brewing Company’s original brewery and tasting room offers rotating craft beers and live music. Nearby, Greenport Harbor Brewery & Restaurant in Peconic provides a larger tasting room and restaurant setting surrounded by fields and farm scenery. For cider lovers, Riverhead Cider House in Calverton features hard ciders made on site in a welcoming tasting room.
Cozy Evenings & Nightlife
As night falls, the Hamptons offer charming spots for film, live music, and cocktails. Sunset Theater in Westhampton Beach is an independent cinema with leather reclining seats and an upstairs cocktail bar, Sunset Social Club, perfect for a cozy date night or an evening with friends. Nearby, the Westhampton Beach Performing Arts Center hosts concerts and shows.
In Sag Harbor, Sag Harbor Cinema blends film and community, with current releases, special screenings, and a bar area for drinks. Bay Street Theater presents plays, comedy, music, and cabaret year-round, while Southampton Playhouse screens classic and contemporary films in an intimate, welcoming setting.
For live music, Stephen Talkhouse in Amagansett is a legendary venue known for vibrant performances and a warm atmosphere. A hidden gem for winter evenings in Sag Harbor is the seasonal pop-up Après Bar located at Sagtown Coffee, serving specialty cocktails and light bites in a cozy setting.
Start the new year with us.
Settle into thoughtfully appointed rooms, unwind by the fireplace, and let the slower rhythm of winter guide your days. Plan a stay shaped by quiet moments, wellness, and the gentle comfort of your winter retreat at Canoe Place Inn.
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