Named one of the prettiest small towns in America by Yankee Magazine, Woodstock, Vermont, is a not-so-hidden gem in Windsor County. With streets lined with 19th-century brick buildings and trees blazing with hues of red, yellow, and orange, it is easy to see why it has become a top-travel destination in both Vermont and New England.
A stroll through Woodstock’s Main Street reveals several boutiques, specialty shops, restaurants, cafes, and inns, the most famous of which being the Woodstock Inn & Resort. For a quick bite to eat, visitors can stop into Mon Vert Cafe for its famous breakfast sandwiches. Another eatery, located right in the heart of downtown Woodstock, is Dr. Coburn’s Tonic, serving American fare and comfort foods.

While in Woodstock, make sure to snap a photo of the Historic Middle Covered Bridge. The centerpiece of Woodstock village, it is located across from the town green and spans the Ottauquechee River. Also in Woodstock is one of the most photographed covered bridges in New England, the Historic Taftsville Covered Bridge, presiding near the Hartland town line.
Just outside Woodstock village is Billings Farm & Museum, which is widely considered to be one of the finest outdoor museums in the country. Catering to visitors of all ages, the museum features a sprawling array of animals, various educational farm exhibits, a restored 19th-century farmhouse, and a gift shop.
Another Woodstock attraction is Marsh-Billings-Rockefeller National Historic Park. Visitors here can indulge themselves in the oldest continuously managed scientific-forest in the United States, with over 20 miles of hiking trails and carriage roads. In addition, guests can learn about conservation history and step into rural Vermont life.
Woodstock’s charm shines through in its unspoiled natural beauty, its historic architecture, and its tranquil way of life. It is the perfect destination for every traveler, and can be enjoyed all year-long, from its lucid colors in the fall and its trees strewn with lights in the winter.
