15 Best Things to Do in Woodstock, Vermont

Nestled in the heart of the Green Mountains, Woodstock Vermont is a charming New England town that embodies the quintessential spirit of rural America. With its picturesque village center, rolling hills, and meandering streams, Woodstock is a haven for those seeking a tranquil retreat from the hustle and bustle of city life.

As you stroll down the town’s quaint Main Street, lined with historic buildings and boutique shops, you can’t help but feel a sense of nostalgia wash over you. From outdoor adventures to cultural attractions, and from farm-to-table cuisine to cozy bed and breakfast inns, Woodstock offers a plethora of things to do and see that will leave you enchanted and inspired.

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Billings Farm & Museum

A working dairy farm and museum, Billings Farm offers visitors a glimpse into Vermont’s agricultural heritage. Explore the farm with its historic barns and gardens, where you can see farm animals up close. The museum highlights the area’s farming history with engaging exhibits and programs, making it fun for all ages.

Marsh-Billings-Rockefeller National Historical Park

This unique national park features a mansion surrounded by beautiful gardens and forested trails. Visitors can tour the mansion to learn about the Rockefeller family’s contributions to conservation and forestry in Vermont. The park’s trails offer stunning views of the changing seasons, particularly during the fall foliage.

Woodstock Village Green

The Village Green is the heart of Woodstock, providing a picturesque setting with charming views of historic buildings and the surrounding hills. It’s a perfect spot for a picnic, and often hosts local events and farmers’ markets. During your visit, enjoy a leisurely stroll around the green and appreciate the quintessential New England architecture.

The Billings Farm & Museum Winter Activities

In winter, Billings Farm offers unique activities such as snowshoeing, cross-country skiing, and winter farm tours. Visitors can engage in hands-on activities like making ice cream and sledding on the farm. The winter events are designed to showcase the farm’s operations during the colder months, making it an enriching experience for all ages.

Woodstock State Forest

Ideal for nature enthusiasts, Woodstock State Forest has miles of trails perfect for hiking, biking, and exploring. The forest is rich with wildlife and offers beautiful views, especially during the fall. In winter, the trails are great for snowmobiling or cross-country skiing.

Teago General Store

This quaint general store offers a taste of authentic Vermont living, providing local goods and delicious snacks. It’s a fantastic spot to grab handmade chocolates, artisanal cheeses, or local crafts. The rustic atmosphere and friendly locals make it a delightful stop while exploring Woodstock.

Woodstock Farmers Market

A local gem, the Woodstock Farmers Market features fresh produce, meats, cheeses, and baked goods sourced from local farms. Visitors can sample artisan foods and shop for unique local products while supporting the community. The market is a great way to experience the local flavor of Vermont.

The Middle Bridge

This iconic covered bridge is one of the most photographed spots in Woodstock. Spanning the Ottauquechee River, it provides a perfect backdrop for stunning photographs, particularly in the autumn. A visit to Middle Bridge is a charming way to appreciate the quintessential New England landscape.

Mount Tom

Hiking to the summit of Mount Tom offers one of the best panoramic views in the area. The trail is relatively short but moderately steep, rewarding hikers with incredible views of Woodstock and the surrounding landscape. It’s an especially popular spot during fall when the foliage transforms the landscape into a breathtaking palette of colors.

Casper’s Ice Cream

A stop at Casper’s Ice Cream is a must for anyone with a sweet tooth. Known for its variety of flavors, this local establishment uses fresh, local ingredients to create their frozen treats. Enjoy your ice cream in a cozy setting right in the heart of Woodstock and discover why it’s a local favorite.

Kedron Valley Inn

The Kedron Valley Inn offers a glimpse into historic New England hospitality with its charming architecture and cozy atmosphere. Guests can enjoy a meal featuring local ingredients in the inn’s restaurant and even stay overnight to soak in the serene surroundings. The inn is a fantastic spot for those looking to experience the local culture and history.

Cloudland Road

Cloudland Road winds through scenic areas of Woodstock and is renowned for its stunning fall foliage. The road is lined with beautiful trees, and each turn reveals picturesque views of the valley and rivers. A leisurely drive or a bike ride along Cloudland Road is a great way to savor the natural beauty of Vermont.

Woodstock History Center

The Woodstock History Center offers fascinating exhibits detailing the town’s rich future and past. Visitors can view artifacts, photographs, and documents that paint a picture of life in Woodstock over the years. It’s an engaging way to learn about the town’s unique character and historical significance.

Simon Pearce Glassblowing

Visiting the Simon Pearce Glassblowing workshop is both an educational and visually stunning experience. Visitors can watch skilled artisans create beautiful glass pieces while enjoying the breathtaking views of the Ottauquechee River. Guests also have the opportunity to shop for exquisite handcrafted glasswork in the attached store.

The Suicide Six Ski Area

Suicide Six is perfect for families seeking winter sports fun, with trails suitable for all skill levels. The small ski area is known for its friendly atmosphere and reasonable prices, making it accessible to casual skiers. In addition to skiing, it also offers snowboarding and tubing for fun-filled winter activities.