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Winter Activities at Rams Head Inn

Escape to The Rams Head Inn this winter for a cozy and vibrant seasonal retreat on Shelter Island. From wine tastings to art exhibits and festive holiday celebrations, there’s an experience waiting for everyone. Embrace the beauty of winter with a lineup of events and activities that make this season unforgettable.

Seasonal Events and Winter Festivities

Celebrate the magic of winter at The Rams Head Inn with seasonal events designed to bring joy and warmth to every guest. Explore nature’s beauty on Shelter Island with activities that celebrate the spirit of winter. Whether you’re a leaf-peeper or looking for festive gatherings, our winter offerings provide the perfect seasonal escape.

Winter Wine Tastings and Culinary Experiences

Warm up with winter wine tastings and specialty culinary experiences at our Shelter Island restaurant. The Rams Head Inn menu features an array of seasonal dishes and wine pairings that showcase local flavors. Indulge in cocktail/mocktail classes, parlor drinks, and guest chef events for unique, seasonal tastes. With a focus on winter flavors, these experiences offer a delicious way to enjoy the chillier months.

Local Art Exhibits and Crafts Workshops

Explore the vibrant local arts scene at Rams Head Inn with our exclusive Shelter Island events. These feature regularly showcased art exhibits and hands-on crafts workshops. We highlight talented local artists, offering a peek into Shelter Island’s creative community and providing an inspiring backdrop for your stay.

Live Music and Fireside Entertainment

Relax by the fire at our Shelter Island hotel with live music each week, featuring an array of genres to warm up your winter nights. Our website and social media channels offer the latest schedule, so you won’t miss an evening of vibrant performances.

Embrace the Beauty of Shelter Island in Winter

Shelter Island is a serene paradise in winter, perfect for quiet exploration and reflection. Surrounded by natural preserves and scenic views, the island offers the ideal backdrop for peaceful strolls and discovering local history.

Island Tours and Historic Sites

Try a self-guided tour of the beautiful Shelter Island, with everything from historical landmarks to hidden scenic gems. The Rams Head Inn team is happy to plan a custom tour matching your interests and physical abilities. With over one-third of the island designated as a natural preserve, there’s no shortage of sights to discover.

Festive Meals at Rams Head Inn Restaurant

Join us on Thanksgiving Day, November 28, for a delightful buffet led by Chef Adam West. Share a meal with friends and family while savoring holiday-inspired dishes that celebrate the season. Reservations are required, so be sure to book in advance for this cherished annual event.

Celebrate Christmas and New Year on Shelter Island

The Rams Head Inn brings the holiday spirit alive with special Christmas and New Year celebrations. From exquisite dining experiences to heartwarming events, enjoy the season’s festivities surrounded by warmth, cheer, and community.

Christmas Tree Lighting and Decoration Events

The Annual Winterfest Tree Lighting on November 30 invites guests to kick off the holiday season with twinkling lights and festive decor. Join us for an evening filled with holiday cheer, and bring the family for a memorable start to the winter celebrations.

Enjoy activities for everyone: decorate cookies with your kids, make sustainable tree ornaments, and sing along with live piano performances. Little ones can sit in on children’s book readings while hot chocolate, hot cider, and s’mores are available for purchase to warm up the festivities.

 

Christmas Dinner and New Year’s Eve Celebrations

Celebrate Christmas Eve at The Rams Head Inn with a seven-course dinner that brings warmth and elegance to the holiday season. Enjoy roasted delights and sweet treats, each dish a handcrafted masterpiece.

On New Year’s Eve, ring in the new year with an exquisite seven-course meal and a festive toast, ensuring a night filled with flavor, joy, and lasting memories. Reservations are recommended for both events to secure your place.

 

Cozy Winter Getaways at The Rams Head Inn

Experience a cozy winter escape at The Rams Head Inn, where the quiet charm of Shelter Island meets the warmth of a fireside retreat. Enjoy the flexibility of self-guided retreats, whether you’re seeking a solo getaway or an inspiring time off with friends to recharge and gain clarity.

Winter is a time for peace, reflection, and inspiration. Relax, unwind, and enjoy all the comforts that make this season the perfect time for a getaway. ​​With its timeless elegance, The Rams Head Inn also offers an ideal setting for an intimate winter wedding on Shelter Island.

Winter Walks with Scenic Views

Take in the natural beauty of Shelter Island with winter walks along our scenic trails. Surrounded by mature trees and serene landscapes, each step is a chance to connect with the peace and quiet of nature.


Don’t miss the chance to feed our friendly baby doll sheep on the property, either! These charming little sheep add a touch of warmth to the winter experience, creating unique moments with nature for visitors of all ages.

Warm Up with Hot Drinks at the Fireplace

After a day of exploring, warm up by the fire with a hot drink. Whether you prefer a classic hot chocolate or a seasonal cocktail, there’s nothing better than curling up with a cozy beverage and enjoying the ambiance of The Rams Head Inn’s inviting atmosphere.

Call The Rams Head Inn Today to Book Your Winter Getaway

Ready to embrace winter’s beauty on Shelter Island? Contact The Rams Head Inn today to book your seasonal stay and experience winter’s charm, warmth, and festive spirit at one of the island’s most beloved retreats.