Discover the Magic of Christmas in Woodstock
As the holiday season approaches, many are searching for a destination that embodies the spirit of New England charm and festive cheer. Woodstock, Vermont, is one such town that transforms into a winter wonderland, captivating visitors with its twinkling lights, snow-covered landscapes, and traditional holiday activities. This is the best guide for Christmas in Woodstock.
During this special time, the village is decked out in garland, and the star on the top of Mount Tom twinkles above the middle covered bridge, creating a truly enchanting atmosphere. You can experience the magic of the season through various activities, from Wassail Weekend to holiday shopping in charming local stores, making it an ideal destination for those seeking an authentic holiday season experience.
The Enchanting Holiday Atmosphere of Woodstock
As you step into Woodstock during the holiday season, you’ll be greeted by a picturesque winter wonderland. The town is transformed into a festive haven, perfect for a holiday getaway.

A Picture-Perfect New England Christmas Setting
Woodstock’s natural beauty creates an idyllic backdrop for a New England Christmas. The village is surrounded by historic architecture, covered bridges, and mountains often dusted with snow, making it a quintessential winter destination.
Festive Decorations and Twinkling Lights
The Woodstock Inn & Resort, located in the heart of the town, is a centerpiece of holiday charm. The courtyard is adorned with elegant decorations, including gingerbread houses and “floating” star lights. Throughout the village, twinkling lights adorn trees and buildings, creating a magical ambiance. The Village Green is also a focal point, with illuminated tree and festive displays.
Experiencing Wassail Weekend: The Heart of Christmas in Woodstock
You can immerse yourself in the magic of Christmas at Woodstock Wassail Weekend. This annual celebration is a spectacle that ties together reverence for the old and the vibrant enthusiasm of the present. The town comes alive with festive décor, carolers in 19th-century attire, and the nostalgic sounds of horse-drawn carriages.

The Historic Wassail Parade and Traditions
The Wassail Weekend Parade is a centerpiece of the celebration, featuring horses and riders adorned in period costumes and festive decorations proceeding around the village green. The parade takes place on both Friday and Saturday, creating a spectacular visual display. The event will go on rain or shine, ensuring a memorable experience.
Holiday Markets and Craft Fairs
During Wassail Weekend, you can explore numerous holiday markets and craft fairs where local artisans showcase handmade gifts, Vermont specialties, and unique treasures. These markets offer a perfect opportunity for holiday shopping while immersing yourself in the local culture.
Carriage Rides and Festive Entertainment
Enjoy horse-drawn carriage rides through the snow-covered streets, offering a romantic and nostalgic way to experience the town’s historic architecture and festive decorations. The weekend also features evening entertainment, including caroling, tree lighting ceremonies, and special performances at venues like the Town Hall Theatre.
As you experience Wassail Weekend, you’ll be surrounded by the true spirit of the holiday season in this charming Vermont town. The community aspect of the celebration, where locals and visitors come together, adds to the warmth and festivity of the event.
Holiday Activities and Attractions
The holiday season in Woodstock is a magical time, filled with enchanting activities and attractions that cater to families and couples alike. You can experience the best of the season by visiting local attractions and participating in festive activities.
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Christmas in Woodstock at Billings Farm & Museum

During December, Billings Farm and Museum features Christmas At The Farm, offering a Victorian Christmas experience. Enjoy olden-day decor, a gingerbread house contest, and candle making. The farm is open every weekend in December and daily from December 21 to January 1, excluding December 24-25. You can enjoy hot cocoa and s’mores by the fireside, meet the animals, and participate in festive activities.
Winter Outdoor Adventures
Woodstock’s winter landscape offers a serene backdrop for outdoor adventures. You can enjoy cross-country skiing through meandering trails or embark on exhilarating snowshoe expeditions. For more adventure, visit Saskadena Six, just minutes from Woodstock, for downhill skiing and snowboarding.
Festive Shopping in Woodstock’s Charming Stores
The village’s charming stores along Main Street and Elm Street offer a delightful shopping experience. You can browse through local artisanal treasures, Vermont goods, and unique gifts at stores like F.H. Gillingham & Sons and Red Wagon Toy Company. Enjoy the twinkling lights and beautifully decorated window displays that add to the festive ambiance.
Planning Your Holiday Visit to Woodstock
Experience the quintessential New England Christmas in Woodstock, a town that embodies the holiday spirit. To make the most of your visit, consider timing your trip during Wassail Weekend, typically the second weekend in December, to experience the town at its festive peak.
Accommodations fill quickly during the holiday season, so it’s wise to book in advance at the Woodstock Inn & Resort or one of the charming bed and breakfasts. A weekend visit allows you to enjoy both village attractions and the surrounding countryside.
Dress warmly for Vermont’s winter weather and plan your itinerary to balance scheduled events with leisure time to explore the village and discover its holiday magic. Consider using the holiday shuttle services during peak weekends for convenient transportation.
Families will enjoy special events like Cookies with Santa and the enchanting atmosphere of Christmas at Billings Farm. Photography enthusiasts will find plenty of opportunities to capture the quintessential Christmas in Woodstock.
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