farm house

Woodstock, Vermont – The Quintessential Fall Small Town

You’ve seen this image a thousand times; (I mean, not this exact image, but this view). Probably the most photographed place in Vermont. For sure the most photgraphed farm in Woodstock, the famous Sleepy Hollow Farm, this is the Vermont quintessential image.

farm house
Sleepy Hollow Farm – Woodstock, VT. By Jake Doucette

Woodstock, Vermont, is home to some of the most beautiful fall vistas in the state. Upon exploring its quaint town center and colorful surroundings, you will immediately fall in love with this small New England village. A state where covered bridges and stores filled with maple products are the norms, Vermont is home to several picturesque towns rich in history. One of these towns is Woodstock, Vermont, located in the Southeast section of the state. Years ago, the Industrial Revolution brought success to Vermont’s manufacturers, and the town became a popular tourism and leisure destination. Today, Woodstock’s tourism industry continues to thrive. The city has fewer than 3,000 people and maintains a free community Wi-Fi service covering most of the village.

The Woodstock Inn is a notable highlight, located right in the center of town. Established by the Rockefeller family, the Inn embodies a classic Vermont style. Originally a tavern built-in 1793, the Inn has undergone several changes and renovations, yet it still upholds 19th-century architecture and rustic feel. Staying at the Inn during the fall allows one to become immersed in plenty of seasonal opportunities, including a Red Barn Dinner series, exclusive resort packages, and the chance to leave the Inn and explore the town on foot.

The town of Woodstock in the fall seems straight out of a postcard. Walking along Central Street provides the opportunity to take in the crisp fall air as you’re surrounded by boutique storefronts and quaint homes covered in pumpkins and fall decor. Visit the Vermont Eclectic Co. to bring home hats, mugs, shirts, and other items, exclusively made by Vermont artists. And no trip to Vermont is complete without stopping by the Vermont Flannel Company for a classic flannel, the perfect fall attire for your trip.

After strolling through town, head over to the Billings Farm and Museum. The farm and museum is the town’s most popular tourist attraction. Similar to the Inn, the land and farmhouse were owned by Laurance Rockefeller and his wife Mary French Rockefeller. The farm and museum include an operating dairy farm and a restored 1890 farmhouse. The museum offers visitors a chance to learn the history of agriculture and conservation in Vermont. During the fall, the farm offers hot apple cider and apple cider donuts to visitors. Visitors can stroll the property to visit the various farm animals and learn about what it takes to run a dairy farm. This year, they are even offering a pumpkin bowling event during the fall! Definitely something to check out.

Across the street from the farm is Marsh-Billings Rockefeller National Historical Park. The park preserves the site where Frederick Billings (Billings Farm & Museum) established a managed forest and a progressive dairy farm. The park contains 555 acres of forest, including trails and century-old carriage roads. Mount Tom is also within the national park’s limits, a small peak standing at 1357 feet high. The mountain contains hiking and running trails, all within walking distance from the town center. To reach the trailhead, visitors often first head to Woodstock’s famous “Middle Bridge.” This 139 foot covered bridge allows visitors to cross by foot, taking in the fall views along the Ottauquechee River. After walking along River Street, hikers will reach the popular trailhead to make the ascent.

Before taking in the panoramic view of Mt. Tom, grab brunch and a coffee at one of the many restaurants and cafes in town. Soulfully Good Cafe (a local favorite) offers delicious brunch options, including fall-inspired dishes such as Pumpkin and Pecan French Toast and Roasted Butternut, Caramelized Onion, and Goat Cheese Quiche. A recommended place to grab a Maple Latte is Mon Vert Cafe. They also have many tasty foods and drink options to indulge in, all made with local, organic ingredients. Both of these cafes are located right in town, on Central Street.

Woodstock is definitely one of Vermont’s most fabulous fall destinations. However, we highly recommend taking a scenic drive during your stay in Vermont to truly take in all of the fall beauty that Vermont has to offer. Whether it’s heading south along Route 106 to view foliage and farmlands or driving around to other local towns and stopping at charming country stores and shops, exploring the open road in Vermont is an enchanting activity on its own.