This Is The Friendliest Small Town In Vermont
With its lively streets, warm-hearted locals, and authentic sense of community, Woodstock, Vermont, is a New England destination that beckons travelers seeking a serene yet vibrant escape. Whether you are a lover of history, an outdoor enthusiast, or someone simply looking for a warm welcome, this small town delivers in every way. From its historic architecture to its buzzing community events, Woodstock exudes a charm that is hard to resist. Join us as we explore what makes Woodstock the friendliest small town in the Green Mountain State.
Location And History
Woodstock is located in central Vermont’s Green Mountains, just a short drive from the Green Mountain National Forest. Its proximity to major highways makes it an easy destination to reach from Burlington, Boston, New York, and beyond. Despite its accessibility, Woodstock retains a quiet, rural ambiance that makes it feel like a hidden gem.
The town was chartered in 1761 and quickly grew into a hub for agriculture, commerce, and culture in the region. Woodstock also played an integral role in the conservation movement with the establishment of the Marsh-Billings-Rockefeller National Historical Park, which celebrates the legacy of sustainable land stewardship. Today, Woodstock’s historic district, with its beautifully preserved 19th-century buildings, showcases its rich heritage and dedication to preservation.
Community Events
Woodstock’s vibrant calendar of community events fosters a spirit of togetherness and offers a warm welcome to visitors. One of the most beloved events is the annual Wassail Weekend, held every December. This festive celebration captures the magic of a traditional New England Christmas with horse-drawn carriage rides, holiday markets, and caroling. Residents and visitors alike come together to enjoy the parade of riders dressed in historical costumes and to admire the twinkling holiday lights that adorn the town.
In addition to Wassail Weekend, Woodstock hosts fun events for every season, including the Covered Bridges Half Marathon (May/June), Independence Day celebration (July), Taste of Woodstock (September), Woodstock Art Festival (September), and Woodstock Apples and Crafts Fair (October). The town also hosts a weekly farmers’ market called Market on the Green from June to October, which features local produce, artisanal goods, and live music.
Cultural Attractions
One of Woodstock’s cultural crown jewels is the Billings Farm & Museum, a working dairy farm and interactive museum that brings Vermont’s agricultural heritage to life. Visitors can meet the farm animals, explore historic barns, and even try their hand at traditional crafts like candle-making or butter-churning.
The Norman Williams Public Library is another cornerstone of Woodstock’s cultural life. Situated in the heart of the village, this stately 1883 stone building is not just a place to borrow books—it is a community hub where locals and visitors gather for lectures, book clubs, and art exhibits. Downtown Woodstock is also home to art galleries, such as Chip Evans Studio, that showcase the works of Vermont’s talented artists.
Local Shops and Eateries
No trip to Woodstock would be complete without experiencing the personal touch offered by its delightful local businesses. One such business is the Woodstock Farmers’ Market, a local grocery store and community gathering spot where you will find fresh produce, artisanal cheeses, and mouthwatering baked goods, many of which are sourced from nearby farms. Another gem is Gillingham’s General Store, which has been serving Woodstock since 1886. This historic shop is a treasure trove of Vermont-made products, from maple syrup to handmade crafts.
When it comes to dining, Worthy Kitchen is a must-visit. Known for its farm-to-table fare and craft beer selection, this casual eatery is a testament to Vermont’s culinary excellence. For a sweet treat, head to Woodstock Scoops, an ice cream parlor that delights visitors with its unique flavors and friendly service. Try the famous Vermont Maple Creemee!
The Great Outdoors
Woodstock is a haven for outdoor enthusiasts, offering a variety of activities that highlight the natural beauty of Vermont. The aforementioned Marsh-Billings-Rockefeller National Historical Park is a perfect starting point for nature lovers. With miles of hiking trails that wind through forests, pastures, and historic landmarks, the park is a stunning example of conservation in action.
For those seeking a more leisurely experience, the Ottauquechee River flows gently through Woodstock, offering opportunities for fishing, kayaking, and scenic picnics. The nearby Quechee Gorge, often referred to as “Vermont’s Little Grand Canyon,” is another must-see. Visitors can hike along the rim for stunning views or descend to the riverbed for a closer look at this natural wonder.
In the winter, Woodstock transforms into a snowy wonderland. The Saskadena Six Ski Area, one of the oldest ski resorts in the United States, offers family-friendly slopes and a relaxed atmosphere. Cross-country skiing and snowshoeing are also popular activities, with trails that cater to all skill levels.
From its rich history and lively community events to its thriving arts scene and breathtaking outdoor attractions, Woodstock embodies the very best of small-town New England. As you stroll along the town’s tree-lined streets, admiring the historic homes and vibrant shops, it is easy to see why so many people fall in love with Woodstock. This is not just a town to visit—it is a town to experience. Once you do, you will understand why it is rightly called the friendliest small town in Vermont.
