Nestled in the heart of Windsor County, Woodstock, Vermont, is a town that feels like it’s been plucked from a storybook. With its quaint Main Street, picturesque village green, and charming covered bridges, it’s a place where history and natural beauty intertwine.Â
Founded in 1761, this town of just over 3,000 residents has a rich past. It was an early commercial hub and became the county seat, attracting artisans, merchants, and influential families who built the elegant homes that still line the streets today.
The town’s unique charm comes from its commitment to preservation, with many of its historic buildings and landscapes meticulously maintained. This isn’t just a place to visit; it’s a place to experience a quieter, more authentic way of life.Â
From exploring Vermont’s only national park to sampling locally made cheese and maple syrup, Woodstock offers an array of activities for every type of traveler. This guide is designed to help you discover the very best of what this magical New England destination has to offer.
Things to Do in Woodstock, VT
1. Billings Farm & Museum
Billings Farm & Museum
Billings Farm & Museum is a working dairy farm and an award-winning outdoor history museum. It offers a glimpse into Vermont’s agricultural heritage and the life of a 19th-century farmer.
The farm, established by Frederick Billings in 1871, combines a dedication to sustainable agriculture with a mission to educate the public. You can see the Jersey cows being milked, watch cheesemaking demonstrations, and learn about the history of the land and its stewards.
Beyond the farm animals and exhibits, the museum features a restored 1890 Farm Manager’s House, which provides a fascinating look at rural life in the late 19th century.
The farm hosts seasonal events and festivals, from sheep shearing in the spring to harvest celebrations in the fall. It’s a fantastic place for families, with hands-on activities and engaging programs that bring history to life.
Plan your visit to coincide with one of the daily demonstrations, such as the cow milking or butter churning, to get a truly immersive experience. These schedules are often posted on their website. The farm store also sells delicious, fresh products, including their own cheese and ice cream, which are a must-try.
Address: 69 Old River Rd, Woodstock, VT 05091
2. Marsh-Billings-Rockefeller National Historical Park
As Vermont’s only national park, Marsh-Billings-Rockefeller is a unique site dedicated to the history of land stewardship and conservation. The park preserves the childhood home of George Perkins Marsh, one of America’s first environmentalists, and later the home of Frederick Billings and then Laurance and Mary Rockefeller. Its 550 acres feature one of the nation’s oldest scientifically managed forests, with a network of carriage roads and trails perfect for hiking.
Visitors can take guided tours of the elegant mansion, which is filled with art and artifacts collected by the Rockefeller family, or simply wander the grounds. The beautiful gardens, including a stunning rock garden and a greenhouse, showcase the Rockefellers’ passion for horticulture. The park’s purpose is to inspire visitors to become stewards of their own land and environment.
The trails are open year-round for hiking and other activities, while the mansion and visitor center operate seasonally from late spring to fall. Be sure to check the park’s schedule for guided tours, as they offer the best insight into the property’s rich history. For a rewarding hike, make your way to the top of Mount Tom for a spectacular view of the village and the surrounding landscape.
Address: 54 Elm St, Woodstock, VT 05091
3. Middle Covered Bridge
The Middle Covered Bridge is one of the most iconic and photographed spots in Woodstock. This picturesque bridge, originally built in 1969, spans the Ottauquechee River and connects the village green with Mountain Avenue. Its classic red siding and white trim are the epitome of New England charm, making it a favorite for both locals and tourists. It’s a pedestrian-only bridge, allowing you to walk across and take in the serene river views without the worry of traffic.
The bridge serves as a beautiful gateway to the village, inviting you to explore the shops and restaurants on Main Street. It’s a perfect spot for a stroll, a photo opportunity, or just a moment of quiet reflection by the water. The sound of the river flowing beneath and the rustic feel of the wooden planks underfoot create a sense of timelessness.
A great tip is to visit the bridge at different times of the day to see how the light changes its appearance. Sunrise and sunset are particularly magical, casting a warm glow on the weathered wood. In the fall, the bridge is surrounded by a symphony of colors, making it a top spot for capturing the iconic Vermont foliage.
Address: Mountain Ave, Woodstock, VT 05091
4. Quechee Gorge
Known as “Vermont’s Little Grand Canyon,” Quechee Gorge is a breathtaking natural wonder located just a short drive from Woodstock. Carved by glacial activity thousands of years ago, the gorge plunges 165 feet, with the Ottauquechee River rushing at the bottom. The view from the Route 4 bridge is spectacular, but for a truly immersive experience, you must explore the trails that wind along the rim and descend into the gorge.
The gorge offers various activities, from hiking and picnicking to swimming in the cool waters of the river below. The trails are well-maintained and provide a mix of easy walks and more challenging sections. The area is also a popular spot for kayaking and fishing. In the winter, the snow-covered cliffs and frozen river create a dramatic and beautiful landscape.
To avoid the crowds, visit early in the morning or on a weekday. While the view from the bridge is easily accessible, be sure to take the time to hike the trails. They offer different perspectives and a greater sense of the gorge’s scale and beauty. Don’t forget to bring sturdy shoes and a camera to capture the stunning views.
Address: 5803 Woodstock Rd, Quechee, VT 05059
5. Sugarbush Farm
A visit to Sugarbush Farm is a treat for the senses and a deep dive into two of Vermont’s most famous products: maple syrup and cheddar cheese. This family-owned farm has been producing these delectable goods for generations. You can take a self-guided tour to see the sugaring operation, from the maple trees with their taps to the sugar house where the sap is boiled down into syrup.
You’ll also learn about the cheese-making process and have the chance to sample a variety of aged cheddars.The farm is set on 550 acres of beautiful rolling hills, with walking trails that take you through the maple woods. It’s a wonderful place to spend a few hours, surrounded by nature and the sweet aroma of maple.
The farm store offers an extensive selection of their cheeses and syrups, as well as other local Vermont products like jams, spreads, and gifts.
The walk to the sugar house and through the woods is a gentle, scenic experience that’s enjoyable for all ages. Don’t be shy about trying the cheese samples—the staff is knowledgeable and happy to help you find your new favorite. Visiting in early spring (late February to early April) is the best time to see the maple syrup production in full swing.
Address: 591 Sugarbush Farm Rd, Woodstock, VT 05091
6. Woodstock History Center
For history buffs, the Woodstock History Center is an essential stop. This museum is dedicated to preserving and sharing the rich history of Woodstock and the surrounding area. Housed in the historic Dana House, a beautiful Federal-style mansion, the center’s exhibits cover everything from the town’s founding and its role as a commercial hub to the lives of its prominent residents.
The center’s collections include period costumes, artifacts, and photographs that tell the story of the town’s evolution. Guided tours of the house are available, offering a deeper understanding of the architecture and the families who lived there. The center also hosts a variety of special events and educational programs throughout the year, which are great for all ages.
Look for the intricate architectural details of the Dana House and the charming garden out back. It’s a quiet and contemplative place that offers a different perspective on Woodstock’s well-preserved past. Be sure to check their website for current exhibit information and opening hours, as they can vary by season.
Address: 26 Elm St, Woodstock, VT 05091
7. F.H. Gillingham & Sons General Store
Stepping into F.H. Gillingham & Sons is like stepping back in time. Founded in 1886, this family-owned general store has been a cornerstone of Woodstock for generations. It’s a true old-fashioned general store, offering everything from hardware and groceries to Vermont-made products, clothing, and unique gifts. The store’s creaky wooden floors and high shelves stocked with countless items create an atmosphere of discovery.
The store’s purpose is not just to sell goods, but to be a community gathering place. It’s a place where you can find a locally made souvenir, pick up a forgotten ingredient for dinner, or simply chat with the friendly staff. It embodies the spirit of a small town, where every item tells a story.
Take your time to explore every aisle, as you never know what you’ll find. Look for the selection of local cheeses, maple syrups, and other Vermont delicacies. It’s the perfect place to buy authentic souvenirs and gifts that truly capture the essence of the state.
Address: 16 Elm St, Woodstock, VT 05091
8. VINS Nature Center (Vermont Institute of Natural Science)
Located in nearby Quechee, the VINS Nature Center is a haven for nature and bird lovers. This conservation and education organization is dedicated to preserving and protecting wild birds and their habitats. The center features a variety of raptors, including eagles, hawks, and owls, many of which are non-releasable due to injury. Visitors can see these magnificent birds up close and learn about their importance to the ecosystem.
The highlight of a visit is the Forest Canopy Walk, an elevated boardwalk that takes you through the treetops, offering a bird’s-eye view of the forest and the Ottauquechee River. The walk is fully accessible and provides a unique perspective on the local flora and fauna. VINS also has a nature shop, a raptor-themed playground, and various educational programs and daily raptor demonstrations.
Check the schedule for the daily bird demonstrations and talks, as they are incredibly informative and engaging. The staff is passionate and knowledgeable, and their enthusiasm is contagious. The canopy walk is a must-do, offering stunning views and a tranquil experience.
Address: 149 Natures Way, Quechee, VT 05059
9. The Woodstock Inn & Resort
The Woodstock Inn & Resort is more than just a place to stay; it’s a destination in itself. With a history that dates back to 1793, the current inn was built in 1969 by Laurance S. Rockefeller. It’s a classic New England resort that combines timeless elegance with modern amenities. The inn’s cozy common areas, grand fireplace, and beautifully landscaped gardens make it a luxurious and relaxing retreat.
The resort offers a wide range of activities for guests and non-guests alike. You can enjoy a round of golf on the Robert Trent Jones Sr.-designed course, play tennis at the Athletic Club, or simply relax at the full-service spa. The inn’s restaurants, including the farm-to-tableRichardson’s Tavern and the fine-diningThe Red Rooster, offer exquisite culinary experiences.
If you’re not staying at the inn, consider booking a dinner reservation or a spa treatment to experience the elegant atmosphere. The resort’s spa is a perfect place for a day of pampering, with services from massages to facials. The grounds are beautifully kept and are lovely for a leisurely stroll even if you are not a guest.
Address: 14 The Green, Woodstock, VT 05091
10. The Lincoln Covered Bridge
Lincoln Covered Bridge
Just outside Woodstock, in the town of West Woodstock, is the charming Lincoln Covered Bridge. This bridge is one of Vermont’s oldest, with a unique lattice truss design and a fascinating history. It was built in 1877 and is one of the few surviving examples of its kind. The bridge crosses the Ottauquechee River and is a must-see for anyone interested in historic architecture.
Unlike the Middle Covered Bridge, the Lincoln Covered Bridge is open to vehicular traffic, making it a living part of the local infrastructure. The rustic feel and the sound of cars crossing the wooden planks create a unique experience. It’s a great spot for a scenic drive and a photo op.
For a great photo, park nearby and take a short walk to capture the bridge’s full beauty. Look for the unique architectural details of the lattice truss. Early morning or late afternoon light is best for photography, and the fall foliage provides a stunning backdrop.
Address: Bridge Rd, West Woodstock, VT 05091
Check out more cities in Vermont. Here is a guide on things to do in Middlebury and things to do in Bennington for a fun time.
11. Woodstock Farmers’ Market
The Woodstock Farmers’ Market is a year-round destination for food lovers. It’s not a traditional outdoor market but a permanent store that offers a vast selection of local and regional products. You’ll find everything from fresh produce and artisanal cheeses to baked goods, prepared foods, and a great selection of beer and wine.
The market prides itself on sourcing high-quality, local ingredients whenever possible, supporting the many small farms and producers in the area. It’s a great place to pick up picnic supplies for a day of exploring, or to grab a delicious sandwich or salad from their prepared food counter. The atmosphere is bustling and friendly, with a true community feel.
The prepared foods section is excellent, with a variety of hot and cold items that are perfect for a quick, delicious meal. Be sure to check out the cheese selection, as it features some of the best artisanal cheeses Vermont has to offer.
Address: 979 W Woodstock Rd, Woodstock, VT 05091
12. The Village Butcher
For a mouthwatering sandwich or a top-quality cut of meat, The Village Butcher is the place to go. This old-fashioned butcher shop and deli has been a local favorite for years, known for its friendly service and high-quality products. They offer a selection of fresh meats, prepared salads, and, most famously, incredible made-to-order sandwiches.
The shop is small but mighty, with a loyal following of locals who appreciate the care and craftsmanship that goes into their products. The sandwiches are generously sized and feature fresh, high-quality ingredients, making them a perfect meal to take on a hike or to enjoy by the river.
The sandwiches are so popular that it’s best to call ahead and place your order, especially during lunchtime, to avoid a wait. They are also known for their homemade soups and salads, which are perfect for a lighter meal.
Address: 34 Elm St, Woodstock, VT 05091
13. The Gallery at the Woodstock History Center
As an extension of the Woodstock History Center, the Gallery is a small but impactful space that showcases local art and historical exhibits. It’s a great way to experience the town’s creative side while also learning about its past. The exhibits change periodically, so there’s always something new to see.
The gallery often features works by local artists, photographers, and artisans, highlighting the vibrant creative community in Woodstock. It’s a wonderful place to appreciate the art that is inspired by the beautiful Vermont landscape. It offers a quiet and thoughtful break from more active pursuits.
Check the center’s website to see what is currently on display. The gallery is a small space, so it’s a quick visit, but it’s a worthwhile one for anyone interested in art and local history.
Address: 26 Elm St, Woodstock, VT 05091
14. Saskadena Six Ski Area
Just a few minutes from the village, Saskadena Six is a historic and family-friendly ski area. It’s one of the oldest ski areas in the country, and it’s known for its laid-back atmosphere and stunning views of the surrounding mountains. It’s a great alternative to the larger, more crowded resorts, offering a more intimate and traditional skiing experience.
While skiing is the main draw in the winter, Saskadena Six also offers mountain biking in the warmer months. The trails are fun and well-maintained, with options for riders of all skill levels. The lodge is a cozy place to relax and enjoy a hot drink or a meal.
If you’re a beginner skier or you’re traveling with children, this is the perfect place to learn and have fun without feeling overwhelmed. It’s a true hidden gem for winter sports enthusiasts. In the summer, the mountain biking trails offer a thrilling way to enjoy the Vermont landscape.
Address: 2470 W Woodstock Rd, Woodstock, VT 05091
15. River Street Cemetery
For a moment of quiet reflection and a connection to the town’s past, visit the historic River Street Cemetery. Located on the bank of the Ottauquechee River, this peaceful cemetery is part of the Vermont African American Heritage Trail. It is the final resting place of eight Black soldiers who served in the Civil War’s all-Black Massachusetts 54th and 55th regiments.
The cemetery is a somber but important reminder of the history of the area and the contributions of African American soldiers. The site is a testament to the town’s deep-rooted history and its place in the larger story of American history. It’s a place to honor and remember those who came before.
Take a moment to read the interpretive signs that tell the stories of these brave soldiers. The peaceful setting by the river makes it a beautiful and contemplative place to visit. The cemetery is always open, and a visit offers a unique and meaningful perspective on the town’s history.
Address: River St, Woodstock, VT 05091
16. Vermont Flannel Company
No trip to Vermont is complete without a piece of authentic flannel. The Vermont Flannel Company is a family-owned business that has been making high-quality, American-made flannel products since 1991. The Woodstock store is a cozy, inviting space where you can browse a wide range of flannel shirts, pants, blankets, and accessories in a variety of colors and patterns.
The company is known for its durable, soft flannel, which is brushed on both sides for extra comfort. Their products are a perfect souvenir or a gift for someone special. The store also offers a unique opportunity to see and feel the quality of the fabric firsthand.
Vermont Flannel Company often has a “seconds” bin with slightly imperfect items at a discounted price. It’s a great way to grab a bargain. The staff is friendly and helpful, so don’t hesitate to ask for recommendations.
Address: 19 Central St, Woodstock, VT 05091
17. The Yankee Bookshop
The Yankee Bookshop is a classic New England independent bookstore that has been serving the Woodstock community since 1935. It’s a charming and cozy place, with stacks of books, a friendly atmosphere, and the inviting smell of paper and ink. The bookstore offers a curated selection of new releases, bestsellers, and a great collection of books on Vermont and New England history and culture.
This is a place to get lost for a while, to browse the shelves, and to discover a new author. The staff is knowledgeable and passionate about books and is always happy to offer a recommendation. It’s a true gem for book lovers and a reminder of the importance of small, independent businesses.
Take your time to explore the different sections and ask the staff for their favorite reads. The bookstore is a great place to pick up a souvenir or a gift. They often have special events, like author signings, so check their social media or website for an updated schedule.
Address: 12 Central St, Woodstock, VT 05091
18. The Spa at The Woodstock Inn
For a day of ultimate relaxation and pampering, book a treatment at The Spa at The Woodstock Inn. The spa offers a luxurious and tranquil escape from the stresses of daily life. With a full menu of services, including massages, facials, body treatments, and manicures/pedicures, you can indulge in a day of self-care.
The spa uses natural, locally sourced products, and the tranquil atmosphere and expert therapists ensure a truly rejuvenating experience. The spa is designed to be a serene sanctuary, with a relaxation room, a sauna, and a beautiful outdoor pool and hot tub area.
It’s highly recommended to book your treatments in advance, especially during peak season, as the spa is a popular destination for both guests and non-guests. A day pass may also be available, allowing you to use the facilities without a treatment.
Address: 14 The Green, Woodstock, VT 05091
19. Simon Pearce
A short drive from Woodstock in Quechee, Simon Pearce is a renowned glassblowing and pottery studio. The flagship store is a beautifully restored mill that sits beside a waterfall, offering a truly unique setting. Visitors can watch master glassblowers at work, transforming molten glass into beautiful, functional works of art.
The mill also houses a beautiful retail store where you can purchase the hand-blown glass and handcrafted pottery. The on-site restaurant, with its stunning views of the waterfall, offers a delicious farm-to-table menu and a chance to dine on the beautiful Simon Pearce tableware.
The best time to visit is on a weekday when it’s less crowded. Arrive early to get a good spot to watch the glassblowing demonstration. If you plan to dine at the restaurant, make a reservation well in advance. The setting is truly magical and the food is excellent.
Address: 1761 Quechee Main St, Quechee, VT 05059
20. Quechee State Park
Quechee State Park
Located near Quechee Gorge, Quechee State Park offers a beautiful natural retreat with a variety of outdoor activities. The park is a great place for camping, picnicking, and hiking. The main attraction is, of course, the access to the gorge, with trails that lead to the river below. The park provides an excellent base camp for exploring the surrounding area.
The park’s location makes it a perfect day trip from Woodstock. You can hike the trails, swim in the river, and simply relax and enjoy the scenic beauty. The park is well-maintained and provides facilities for a comfortable visit.
The park can get very crowded during the summer and on weekends. Arrive early to secure a parking spot and avoid the rush. Bring a picnic to enjoy by the river or at one of the picnic tables. The trails are well-marked and offer a great workout with rewarding views.
Address: 5800 Woodstock Rd, Quechee, VT 05059
Conclusion
Woodstock is more than just a pretty town; it’s a living piece of New England history. Its cobblestone streets, charming covered bridges, and beautifully preserved architecture create an atmosphere that feels both timeless and welcoming. This is a place where the pace of life slows down, allowing you to connect with nature, history, and a vibrant local culture.
From the rolling hills of its national park to the bustling heart of its village green, Woodstock offers a unique blend of outdoor adventure and cultural richness. Whether you’re hiking a mountain trail, exploring a historic farm, or simply enjoying a delicious meal at a local cafe, you’ll find that Woodstock leaves a lasting impression. Come and discover this magical town for yourself. Create your own memories and find a little piece of your heart in Woodstock, Vermont.
