Looking for ways to make your winter memorable? Head to the Hamptons, where a blend of holiday charm, outdoor adventures, and cozy gatherings wait. From family-friendly activities to festive events, these seven must-visit destinations will help you embrace the holiday spirit out east.
Experience the Magic of the Montauk Holiday Fair
Mark your calendars for the Third Annual Magic of Montauk Holiday Fair on December 14 and 15 (2-7 p.m.). This free event brings coastal charm and holiday magic to Montauk’s town green with dazzling lights, live music, and unique vendors.
Shop handmade crafts, indulge in festival treats, or warm up with a hot cocoa contest. Adults can enjoy wine or beer while kids explore snow-filled igloos and other activities. New this year is a glass-blowing demonstration where artisans craft stunning ornaments.
Jessica Dye of the Montauk Chamber of Commerce describes the event as a growing community favorite, adding more yearly festive surprises. “We grew tremendously with the number of people who attended, so we wanted to extend it to offer more for the community and visitors, and to help support any businesses that are open,” Dye said. “We hope everyone can enjoy it over both days.”
Location: Town Green, Montauk
Explore Holiday Magic at Marders in Bridgehampton
Marders is a 33-acre holiday wonderland nestled behind the Bridgehampton Commons. The scenic spot offers festive activities to brighten your winter days.
Stop by the Garden Shop, housed in a charming 19th-century barn. While there, you can browse glittery ornaments and rustic holiday decor.
Join their holiday wreath workshops on December 8 and 15 for hands-on fun. Don’t miss the Steve Shaughnessy Trio musical performances on December 1 or the chance to snap a selfie with Santa and Birds of Prey on December 14.
Location: 120 Snake Hollow Road, Bridgehampton.
Savor Wine and Comfort at Wölffer Estate in Sagaponack
Warm up on a chilly evening with a wine flight at Wölffer Estate’s cozy Tasting Room. Enjoy savory charcuterie, cheese platters, and breathtaking vineyard views while sitting on tufted leather couches beneath rustic wood beams.
Whether you’re sampling the Pearly Chardonnay 2021 or the Finca Wölffer Brau, there’s no shortage of options to please your palate. The Tasting Room is open daily, and fun winter events enhance your visit.
Location: 139 Sagg Road, Sagaponack
Take Aim at Suffolk County Shooting Sports
For outdoor enthusiasts, the Suffolk County Trap, Skeet & Sporting Clays facility offers a rustic escape. The scenic spot is situated west of Manorville and features 14 Skeet Fields, four trap fields, and two sporting clay courses for beginners and seasoned shooters.
Rent a golf cart to get around the grounds or enjoy brisk walks along the wooden paths. Remember to wear sturdy boots, especially after a rainy day, as the trails can get muddy.
Location: 165 Gerard Road, Yaphank
Meet Mrs. Claus at the Holiday Open House in East Hampton
The Ladies Village Improvement Society’s annual holiday open house is a must for families. Held at the historic Gardiner Brown House, this December 7 event (1-4 p.m.) invites kids to share their Christmas list with none other than Mrs. Claus.
Children will receive special holiday treats while enjoying a festive afternoon in a cozy, welcoming setting. This time-honored tradition captures the heart of the holiday season.
Location: 95 Main Street, East Hampton
Enjoy a Christmas Tree Lighting in Hampton Bays
Nothing evokes the holiday spirit like a traditional Christmas tree lighting. On December 5, the Canoe Place Inn & Cottages hosts this delightful event, complete with live holiday music, a visit from Santa, and plenty of seasonal cheer.
Gather your loved ones for this magical evening and make lasting memories.
Location: 239 E. Montauk Highway, Hampton Bays
Celebrate at the Parade of Lights in Southampton
Kick off the holidays with the dancing Parade of Lights and Christmas Tree Lighting at Agawam Park on November 30. This annual celebration features Carolers, whimsical floats, ice cream trucks, and beautifully decorated fire trucks.
Bring the whole family to soak up the atmosphere and start your holiday season with joy and community spirit.
Location: 51 Pond Lane, Southampton.
Whether you’re strolling through Montauk’s holiday fair or cozying up with a glass of wine at Wölffer Estate, the Hamptons offer a treasure trove of winter adventures.
Bundle up, bring your family, and experience this beautiful coastal destination.
