The Hamptons may shine brightest in the summer, but winter reveals a side of this iconic destination that’s equally captivating. The crisp air, serene landscapes, and cozy indoor experiences create the perfect setting for a magical getaway. Whether you’re an outdoor enthusiast or someone who prefers to indulge in luxurious relaxation by the fireplace, the Hamptons in winter offers plenty to enjoy. Here’s your ultimate guide to making the most of the season in this enchanting locale.
Maidstone Park, East Hampton
1. Glide Into Winter Fun with Ice Skating
Ice skating is a quintessential winter activity, and the Hamptons doesn’t disappoint when it comes to charming rinks with stunning backdrops.
Buckskill Winter Club (East Hampton): This outdoor rink is a local favorite, offering a picture-perfect setting surrounded by snow-dusted trees. Ice skating lessons are available for beginners, and their cozy clubhouse serves hot cocoa to thaw you out post-skate.
Southampton Ice Rink: A family-friendly spot that’s ideal for all ages, this rink provides rental skates and an inviting atmosphere where visitors can enjoy afternoon gliding sessions or themed skating events under twinkling lights.
Pro Tip: Visit early in the day to avoid crowds, especially on weekends. Don’t forget your gloves and scarf—the coastal breeze can be brisk on the ice!
2. Explore the Outdoors with Winter Hiking
Winter transforms the Hamptons’ nature trails into peaceful escapes, offering breathtaking views you won’t experience during the busy months. Hiking through fresh snow or frosty woodlands is a magical way to reconnect with nature.
The Walking Dunes (Hither Hills State Park, Montauk): Discover these stunning sand dunes shimmering under a dusting of frost. The loop trail offers incredible views of the Atlantic Ocean and is perfect for a brisk, energizing hike.
Mashomack Preserve (Shelter Island): This extensive preserve comes alive in winter, with leafless trees revealing gorgeous vistas. Bundle up and explore its serene trails teeming with winter wildlife like deer and foxes.
Shadmoor State Park (Montauk): For a coastal winter hike, this scenic spot is unbeatable. Its trails lead to dramatic cliffs and panoramic ocean views that offer a rugged, windswept beauty only winter can deliver.
Pro Tip: Dress in layers and wear waterproof boots—the trails can get icy or muddy. Pack a thermos of tea or coffee to enjoy while soaking up the views.
3. Cozy Up Indoors with Hamptons Charm
When the cold calls for comfort, the Hamptons offers no shortage of luxurious indoor experiences that wrap you in warmth and relaxation.
Wineries and Vineyards: Winter is the perfect time to visit local wineries like Wölffer Estate Vineyard in Sagaponack. Enjoy tastings of mulled wine alongside cozy fireplaces overlooking the vineyard’s serene winter landscape.
The Baker House 1650 (East Hampton): This charming boutique inn offers the ultimate indoor respite. With crackling fires and plush furnishings, it’s a great spot to enjoy baked treats or indulge in their day spa offerings.
Art and Culture Stops: The winter season allows for a quieter stroll through the Hamptons' cultural landmarks. Visit the Parrish Art Museum in Water Mill to soak in modern art, or explore Guild Hall in East Hampton for intimate exhibits and seasonal performances.
Pro Tip: Reserve your spots in advance for tastings or wellness treatments. Winter weekends can still draw loyal Hamptons fans seeking escape.
4. Indulge in Seasonal Dining Delights
Winter is a foodie’s dream in the Hamptons, with restaurants featuring seasonal menus that celebrate locally sourced ingredients.
Tutto Il Giorno (Southampton): Cozy up with comfort dishes like butternut squash soup or Tutto Parmigiana in a cozy dining room. This iconic spot offers a touch of elegance perfect for the season.
Nick & Toni’s (East Hampton): A Hamptons staple, this restaurant is known for its farm-to-table cuisine. Their wood-fired pizzas and seasonal specials make for the ultimate winter comfort food.
Harvest on Fort Pond (Montauk): Known for its family-style meals, this Montauk gem specializes in satisfying dishes like braised short ribs and roasted vegetables—perfect fuel after a day outdoors.
Pro Tip: Ask your server for wine or cocktail pairings. Many eateries feature local vineyard selections ideal for enhancing your dining experience.
5. Winter Events and Festivals
The Hamptons might be quieter in winter, but it comes alive with events that celebrate the season.
HarborFrost (Sag Harbor): Usually the first week in February, Sag Harbor hosts this winter festival with ice sculptors, fireworks and live music around town.
Montauk Halfway to Summer Party (Montauk): Yes, a Montauk Party in the dead of winter. Held annually at the Montauket in February, keep and eye out for this fun winter event.
Annual Candlelight Tours (Southampton): These history tours take you through centuries-old estates decked out in holiday décor, illuminating the Hamptons' rich heritage and timeless charm.
Pro Tip: Always check event schedules ahead of time—weather or crowd limitations can affect winter events.
6. Treat Yourself to a Staycation
There’s something special about escaping to the Hamptons in the off-season, when everything slows down and the area shines with tranquility. Book a stay at:
Gurney's Montauk Resort: Famous for its luxury and oceanfront views, Gurney’s offers winter spa specials, cozy igloo dining, and even a heated indoor pool for a dreamy winter retreat.
Baron’s Cove (Sag Harbor): This charming harborfront inn boasts a seasonal menu, roaring fireplaces, and delightful winter activities for guests. Great spot to stop in for a drink even if you don’t stay the night.
Naturopathica (East Hampton): A luxurious spa with indulgent treatments perfect for a cold winter day.
Pro Tip: Plan midweek stays for the best rates and a more exclusive experience in otherwise popular spots.
The Charm of Winter in the Hamptons
The Hamptons in winter is a season of contrasts—silent snow-covered trails balanced with the cozy hum of bustling inns and markets. It’s an opportunity to experience this iconic destination in a whole new way, appreciating its natural beauty and luxurious touches without the summer crowds.
Whether you're gliding across an ice rink, hiking beneath frost-covered canopies, or unwinding with a glass of local wine by the fire, the Hamptons promises a winter retreat unlike any other. Pack your favorite sweaters, plan your itinerary, and get ready to savor the magic of this season—it’s what makes the Hamptons unforgettable year-round.