Thanksgiving in the Hamptons is more than just a meal—it’s an opportunity to bask in the beauty of the season, enjoy cozy gatherings, and indulge in some of the region’s finest wines and brews. If you’re heading to the Hamptons for the holiday weekend, we’ve crafted a curated itinerary that blends the charm of Thanksgiving with the best wineries, breweries, and seasonal experiences the area has to offer.
Friday: Arrival and First Sips
Afternoon
Check-in and settle down at a cozy boutique inn or rental. Options like The Maidstone or The Baker House in East Hampton or a charming cottage in Sag Harbor will instantly set the tone for a relaxed weekend.
After unpacking, kick things off with a trip to Wölffer Estate Vineyard in Sagaponack. Known for its picturesque vineyard views and sophisticated atmosphere, Wölffer is the perfect place to toast the start of your weekend. Sip their signature rosé (yes, it’s fabulous year-round) or try their seasonal selections like the rich and spicy Cabernet Franc.
Evening
Head to The American Hotel in Sag Harbor, a local gem balancing fine dining and historic charm. Their extensive wine list and seasonal menu—featuring dishes like roasted duck or pumpkin risotto—make it a quintessential Hamptons dining experience.
Saturday: Festive Fun, Wine, and Brews
Morning
Kick off Saturday with festive cheer at the East Hampton Gardens Holiday Open House, happening from 10 AM to 2 PM. This family-friendly event offers holiday magic with face painting, pony rides, a visit from Santa, and the opening of their enchanting holiday shop. Whether you’re young or young at heart, this open house is the perfect way to soak in the festive atmosphere. Admire the beautiful decor, shop for holiday treasures, and enjoy the seasonal spirit before heading to your next stop.
Afternoon
After the open house, head to Channing Daughters Winery in Bridgehampton. This celebrated winery offers unique, artisanal wines crafted with care. Try their seasonal tastings (like Blaufränkisch or rustic reds), and book ahead if possible for a guided experience.
Next, it’s time to explore local beer. Stop by Montauk Brewing Company, where their small-batch, seasonal beers shine. Try the Pumpkin Ale or Driftwood Ale while enjoying the cozy tasting room vibe.
Sunday: Thanksgiving Traditions with a Twist
Morning
After breakfast, take a scenic drive to Shinn Estate Vineyards in Mattituck. Just a bit farther out, but absolutely worth the trip, this North Fork staple exudes rustic charm. Their tasting room will likely feature cozy, holiday-ready pours like Merlot blends or mulled wine to warm your spirit.
Midday
For a laid-back lunch, stop by Love Lane Kitchen in Mattituck. This welcoming farm-to-table café offers seasonal comfort food like squash soup or hearty sandwiches made with local ingredients.
Afternoon
Before heading back, swing by Greenport Harbor Brewing Company, located in a renovated firehouse in Greenport. Sample their inventive craft beers, such as Harbor Ale or Black Duck Porter. Stick around for a relaxed afternoon of tasting and light fare—perfect for soaking in the easygoing Hamptons vibe one last time.
Evening
Wrap up the weekend with a waterfront sunset walk at Main Beach in East Hampton or Coopers Beach in Southampton. These beach landscapes take on a magical quality in the quiet fall months, offering breathtaking views and a peaceful close to your holiday escape.
Additional Thanksgiving Weekend Highlights
Thanksgiving Market at Hayground School (Saturday)
Wander through this community market featuring local vendors selling baked goods, crafts, and holiday gifts. It’s a great place to stock up on festive treats or bring home a taste of the Hamptons.Outdoor Ice Skating at Southampton Ice Rink
Get in the wintry spirit early with a twirl around the rink under the cool November sky.