Woodstock, Vermont, is often called one of New England’s most charming villages. With its covered bridges, tree-lined streets, and deep connection to Vermont’s history, it’s the kind of place that makes you feel like you’ve stepped into a storybook. At the heart of this history is The Jackson, a landmark that has welcomed travelers to Woodstock for generations.
A Town with a Storied Past
Woodstock’s roots stretch back to the 18th century, when it became a hub for farming, milling, and later, tourism. Wealthy families from Boston and New York were drawn to the Green Mountains in the 1800s for fresh air, scenic beauty, and summer retreats. Their influence can still be seen today in the town’s grand homes, cultural institutions, and dedication to preserving its natural landscape.
The arrival of the railroad in the mid-1800s made Woodstock even more accessible. Visitors flocked here not only for the views but also for the community’s welcoming spirit and its balance of sophistication and simplicity. Over time, Woodstock became a model for small-town New England charm, blending history, culture, and recreation into one destination.
The Jackson’s Place in Woodstock History
The Jackson has long been part of Woodstock’s fabric. Originally established as an inn that catered to both travelers and townsfolk, it quickly became more than just a place to stay—it was a gathering spot. Generations of guests have enjoyed meals, celebrations, and quiet moments within its walls.
Throughout the years, The Jackson has evolved with the times while staying true to its roots. Renovations have refreshed the interiors, menus, and amenities, but the inn has always kept its Vermont character intact. Guests return year after year because The Jackson offers something rare: a connection to the past without sacrificing the comforts of the present.
Why Woodstock, VT Is Special
Part of what makes The Jackson so unique is its location in downtown Woodstock. Guests step outside the inn and are immediately surrounded by everything that defines Vermont living. Just steps away are local shops, artisan galleries, and restaurants showcasing farm-to-table cuisine.
Woodstock is also home to cultural landmarks like the Billings Farm & Museum and the Marsh-Billings-Rockefeller National Historical Park—the only national park to focus on the history of conservation. Pair that with seasonal traditions like fall foliage drives, winter skiing, and summer hiking, and it’s no wonder Woodstock is considered a year-round destination.
A Modern Revival of Tradition
Recent renovations at The Jackson were made with care to honor its historic role in Woodstock. Guests will find refreshed rooms, a welcoming lobby, and thoughtful amenities that nod to Vermont’s heritage. From locally inspired menus to design details that highlight craftsmanship, every update reflects both the history of the inn and the spirit of the town.
Breakfast, once a cherished tradition at The Jackson, has made its return—giving guests the perfect start to a day exploring Woodstock. Evenings are marked by warm hospitality and a renewed sense of community, reminding visitors why inns like The Jackson are so central to New England’s character.
Plan Your Visit
Whether it’s your first trip to Woodstock or a return to a favorite destination, The Jackson is more than a place to rest—it’s a chance to experience history, hospitality, and the heart of Vermont. Staying here means walking the same streets generations of travelers once strolled, connecting with the same landscapes that inspired conservation pioneers, and becoming part of a story that continues to unfold.
