20 Best Things To Do In Woodstock, Vermont

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Looking for the best things to do in Woodstock? We have you covered with this ultimate guide to the 20 best things to do in Woodstock, Vermont!

Welcome to Woodstock, Vermont, a charming New England town that embodies the essence of timeless beauty, warm hospitality, and rich cultural heritage. Nestled amidst the picturesque landscapes of the Green Mountains, Woodstock offers visitors a delightful escape from the hustle and bustle of modern life. With its historic buildings, quaint village green, and a wealth of cultural and outdoor attractions, this enchanting town beckons travelers to immerse themselves in its captivating charm and discover the many wonders it has to offer. 

Join us as we embark on a journey through the heart of Woodstock, exploring its vibrant downtown, iconic covered bridges, scenic trails, and local treasures that make it a destination unlike any other. We hope this blog post serves as the ultimate guide to Woodstock, Vermont. Below you will find the 20 best things to do in Woodstock, Vermont:

1. Enjoy a true Vermont maple experience at Sugarbush Farm

Photo by @tomriley on Instagram

Sugarbush Farm is a beloved destination that offers visitors a delightful taste of Vermont’s rich agricultural heritage. This family-owned farm is renowned for its award-winning maple syrup and artisanal cheese. As you venture onto the farm’s scenic trails, you’ll be surrounded by the beauty of the Vermont countryside, dotted with sugar maple trees that produce the sweet, golden syrup. The farm offers informative and engaging tours, where visitors can learn about the maple sugaring process, from tapping the trees to boiling the sap into maple syrup. 

The tasting room is another highlight, where guests can sample a variety of maple products, including different grades of syrup, maple candies, and other delectable treats. Additionally, the farm’s cheese-making operation provides a chance to taste a selection of handcrafted cheeses made on-site. With its warm hospitality and authentic farm experience, a visit to Sugarbush Farm is a delightful and memorable journey that captures the essence of Vermont’s rural charm and culinary traditions.

Learn more about Sugarbush Farm

2. Cross the magical Taftsville Covered Bridge

Photo by @tomriley on Instagram

The Taftsville Covered Bridge in Woodstock, Vermont, is a historic gem that exudes classic New England charm and serves as a living testament to the region’s rich heritage. Built in 1836, this iconic bridge spans gracefully over the Ottauquechee River, creating a picture-perfect scene that captures the imagination of visitors. With its striking red exterior and Town lattice truss design, the Taftsville Covered Bridge is a beloved landmark that has withstood the test of time.

Learn more about the Taftsville Covered Bridge

3. Explore the Marsh-Billings-Rockefeller National Historical Park

“Mansion in spring 2017” by Marsh-Billings-Rockefeller National Historical Par is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/2.0/

The Marsh-Billings-Rockefeller National Historical Park in Woodstock, Vermont, is a captivating destination that offers a glimpse into the rich history and conservation legacy of the region. Situated on 550 acres of pristine Vermont landscapes, this park is a living testament to the stewardship and dedication of its former owners, who played a pivotal role in preserving its natural beauty. 

The park comprises three historic properties—the 19th-century Marsh-Billings-Rockefeller Mansion, the working Billings Farm with its Jersey cows and agricultural exhibits, and the picturesque gardens and trails that wind through the property. Visitors can immerse themselves in the stories of the Marsh, Billings, and Rockefeller families, who were pioneers in the conservation movement and played a significant role in shaping the region’s natural landscapes. A visit to the Marsh-Billings-Rockefeller National Historical Park is a journey through time and a celebration of Vermont’s unique cultural heritage and the importance of preserving its natural beauty for future generations.

4. Learn about Woodstock farming history at the Billings Farm and Museum 

“Billings Farm-8” by skyobrienpics is licensed under CC BY-NC 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc/2.0/

The Billings Farm and Museum is a delightful and immersive experience that takes visitors on a journey through the rich agricultural heritage of the region. Founded in 1871, this working dairy farm is a living testament to the dedication and innovation of the Billings family, who played a crucial role in Vermont’s farming history. 

The museum offers engaging exhibits and interactive displays that showcase the evolution of Vermont’s rural life, from the 19th century to the present day. Visitors can explore the beautifully preserved farmhouse, learn about traditional farming practices, and even participate in hands-on activities such as butter churning and milking demonstrations. 

The farm’s picturesque setting provides a perfect backdrop for observing Jersey cows grazing in the fields and other farm animals that call the property home. With its authentic representation of Vermont’s farming heritage, the Billings Farm and Museum offers an enriching and educational experience for visitors of all ages, highlighting the importance of agriculture in shaping the cultural and economic landscape of Vermont.

5. Visit the artisans at Farmhouse Pottery

Farmhouse Pottery in Woodstock, Vermont, is a haven for artisanal craftsmanship and timeless design. Nestled in the picturesque countryside, this charming pottery studio and retail store embodies the essence of Vermont’s creative spirit. The pottery at Farmhouse Pottery is handmade with care and attention to detail, reflecting a rustic yet refined aesthetic. Each piece is crafted using traditional techniques and locally sourced materials, resulting in elegant and durable stoneware that is both functional and beautiful. 

The retail store showcases a curated selection of pottery and home goods, offering visitors the chance to take home a piece of Vermont’s creative legacy. A visit to Farmhouse Pottery is not only a shopping experience but also an opportunity to witness the artistry and craftsmanship that goes into each unique creation. On any given day, there are several experts throwing pottery on wheels in a room adjacent to the retail room. Whether you’re an art enthusiast or simply appreciate the beauty of handmade pottery, Farmhouse Pottery in Woodstock is a delightful destination that celebrates the creativity and artistry of Vermont’s artisan community.

6. Grab a sandwich, pastry, and snacks at the Woodstock Farmers Market

The Woodstock Farmers Market in Woodstock, Vermont, is a beloved local institution that embodies the essence of Vermont’s agricultural bounty. This bustling market is a vibrant gathering place where residents and visitors alike come together to celebrate and support local farmers, artisans, and producers. The market stocks hundreds of high-quality products and many local products. Visitors can shop for great fruits, veggies, snacks, and beverages all crafted nearby. The market is also known for its deli. The deli crafts handmade sandwiches along with dozens of prepared foods like roasted chicken, salads, and much more. Oh and the bakery at the Woodstock Farmers Market is pretty legendary too. Be sure to grab one of their massive chocolate chip cookies which are probably bigger than your face.

7. Photograph the legendary Sleepy Hollow Farm

Photo by @engineer.with.a.hobby on Instagram

Photographing Sleepy Hollow Farm in Pomfret, Vermont, is an enchanting and awe-inspiring experience that transports photographers to a picturesque landscape straight out of a storybook. This iconic farm, with its historic barn, rolling green hills, and charming white farmhouse, epitomizes the timeless beauty of rural Vermont. Whether you’re a professional photographer or an amateur enthusiast, Sleepy Hollow Farm invites you to unleash your creativity and witness the magic of capturing the natural beauty and rich history of this beloved Vermont landmark through the lens of your camera.

Learn more about Sleepy Hollow Farm

8. Sip on a fresh coffee and a homemade snack at Mon Vert Cafe

Mon Vert Cafe in Woodstock, Vermont, is a charming and inviting haven that embodies the spirit of community and the love for delicious food. This cozy cafe, which translates to “My Green Cafe” in French, embraces a farm-to-table ethos and a commitment to sourcing locally sourced, organic ingredients. Nestled in the heart of Woodstock, Mon Vert Cafe’s warm and welcoming ambiance makes it a popular gathering spot for locals and visitors alike. 

The menu showcases a delectable selection of breakfast and lunch options, including mouthwatering sandwiches, salads, and savory quiches, all made with the freshest and finest ingredients. The cafe’s passion for sourcing local ingredients is evident, some local companies they highlight are Back Roads Granola (Brattleboro, Vermont), King Arthur Flour (Norwich, Vermont), Plymouth Cheese (Plymouth, Vermont), Vermont Coffee (Middlebury, Vermont), Red Hen Baking (Middlesex, Vermont), and many many more. Whether you’re looking for a leisurely brunch, a quick bite, or simply a relaxing spot to savor a cup of artisanal coffee, Mon Vert Cafe offers a delightful culinary experience that celebrates the essence of Vermont’s natural beauty and community-focused spirit.

9. Get pampered at the Woodstock Inn spa

The Woodstock Inn Spa in Woodstock, Vermont, is a serene and indulgent retreat that promises relaxation and rejuvenation amidst the beauty of Vermont’s countryside. Nestled in the heart of the charming town of Woodstock, this luxurious spa offers a wide range of pampering treatments and wellness experiences that cater to guests’ every need. From soothing massages and facials to body scrubs and aromatherapy, the spa’s experienced therapists provide personalized care to ensure a truly blissful experience. The spa’s tranquil ambiance, with its elegant décor and natural elements, creates a calming oasis where guests can unwind and escape from the stresses of everyday life. 

In addition to its extensive menu of spa treatments, The Woodstock Inn Spa also features a fitness center, a steam room, and an outdoor relaxation pool, offering guests a holistic approach to health and well-being. Whether you’re seeking a peaceful escape or a luxurious spa day, The Woodstock Inn Spa invites visitors to indulge in a rejuvenating experience that celebrates the essence of Vermont’s hospitality and natural beauty.

10. Ski at Saskadena Six (formerly known as Suicide Six)

Suicide Six ski mountain in Vermont is a beloved winter destination that combines a rich history with a family-friendly atmosphere. Located near the picturesque town of Woodstock, Suicide Six has been providing winter thrills to visitors since 1936, making it one of the oldest ski areas in the United States. Despite its name, the mountain offers a wide range of terrain suitable for skiers and snowboarders of all skill levels, from gentle beginner slopes to challenging trails for more experienced riders. The resort’s welcoming ambiance and small-town charm make it a popular choice for families and those seeking a laid-back skiing experience. In addition to its ski and snowboarding offerings, Suicide Six also features a tubing park, cross-country skiing, and snowshoeing trails, ensuring there’s something for everyone to enjoy during the winter months. With its scenic vistas, well-groomed trails, and friendly staff, Suicide Six ski mountain offers a timeless winter escape that captures the essence of Vermont’s outdoor winter wonderland.

11. Shop downtown Woodstock

“Woodstock, Vermont” by Jasperdo is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/2.0/

Shopping in downtown Woodstock, Vermont, is a delightful and unique experience that captures the essence of this charming New England town. With its historic buildings and picturesque village green as a backdrop, the streets are lined with a variety of boutiques, art galleries, and specialty shops, each offering its own distinct treasures. Visitors can browse through an array of locally made crafts, artisanal products, and unique souvenirs that celebrate Vermont’s rich cultural heritage. 

From handcrafted jewelry and pottery to gourmet foods and farm-to-table delights, downtown Woodstock’s shops are a haven for those seeking one-of-a-kind gifts and keepsakes. The warm and friendly atmosphere, coupled with the personalized service from local shop owners, creates a welcoming experience that makes shopping in downtown Woodstock a truly memorable and enjoyable outing. Whether you’re searching for a piece of Vermont’s artistic spirit or simply looking to explore the town’s vibrant retail scene, shopping in downtown Woodstock is a delightful journey of discovery through the heart of this picturesque Vermont town.

12. Hike up Mount Tom for sweeping views

“Fall Hikers on Mt Tom” by Marsh-Billings-Rockefeller National Historical Par is licensed under CC BY-NC-ND 2.0. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/2.0/

Hiking up Mount Tom in Woodstock, Vermont, is a rewarding and invigorating outdoor adventure that offers breathtaking views and a sense of accomplishment. The trailhead, conveniently located near the town center, begins the ascent through a serene forest filled with lush foliage and the sounds of nature. As hikers make their way up the well-marked path, the journey becomes more invigorating, passing over rocky terrain and gentle inclines. Along the way, hikers are treated to glimpses of the surrounding valleys and the picturesque town below. Upon reaching the summit, a breathtaking panorama of Vermont’s rolling hills and the charming town of Woodstock awaits, providing a perfect setting for a well-deserved rest and some memorable photographs. Whether you’re a seasoned hiker or just beginning to explore the wonders of nature, the experience of hiking up Mount Tom is a memorable and enriching journey that captures the essence of Vermont’s natural beauty.

13. Admire the historic Woodstock Middle Covered Bridge

Photo by @tomriley on Instagram

The Woodstock Middle Covered Bridge in Woodstock, Vermont, is a charming and historic landmark that evokes the timeless beauty of New England’s covered bridges. Originally constructed in 1969, this picturesque bridge spans across the Ottauquechee River, connecting the village of Woodstock with the River Street neighborhood. The bridge’s natural exterior, lattice truss design, and weathered wooden planks exude a sense of rustic elegance, making it a favorite subject for photographers and a beloved symbol of Vermont’s heritage. 

As visitors stroll through the bridge’s covered walkway, they are immersed in a nostalgic journey through time, surrounded by the gentle sounds of the river below and the picturesque views of Vermont’s countryside. The Woodstock Middle Covered Bridge serves not only as a practical means of transportation but also as a cherished piece of history that embodies the enduring charm and traditions of this quaint New England town.

Learn more about the Woodstock Middle Covered Bridge

14. Take a walk at the Eshqua Bog Natural Area

The Eshqua Bog Natural Area in Woodstock, Vermont, is a captivating and ecologically significant wetland that offers visitors a unique glimpse into the natural wonders of the region. Situated just outside the town center, this 41-acre natural area is a haven for nature enthusiasts and wildlife observers. The bog’s diverse and fragile ecosystem, characterized by sphagnum moss, tamarack trees, and wildflowers, provides a habitat for a variety of plant and animal species, including rare and endangered ones. 

A boardwalk trail meanders through the bog, allowing visitors to explore its rich biodiversity and observe unique plant life up close. Birdwatchers will be delighted by the opportunity to spot migratory and resident bird species, such as warblers, woodpeckers, and waterfowl. With its serene ambiance and captivating landscapes, the Eshqua Bog Natural Area offers a peaceful escape and a chance to connect with the natural beauty and conservation efforts of Vermont’s wilderness. Today, the natural area is managed by The Nature Conservancy

15. Dine at Worthy Kitchen

The Worthy Kitchen in Woodstock, Vermont, is a beloved culinary gem that showcases the best of Vermont’s farm-to-table cuisine in a casual and welcoming setting. Located just outside of downtown, this restaurant combines a passion for local ingredients with a creative flair, offering a menu that celebrates the flavors of the region. From their mouthwatering burgers made with locally raised beef to their delectable vegetarian options and artisanal craft beers, The Worthy Kitchen’s menu caters to a diverse range of tastes and preferences. 

The restaurant’s rustic and inviting atmosphere, with its reclaimed wood decor and friendly staff, creates a warm and welcoming ambiance for guests to savor their meals. Whether you’re a food enthusiast seeking a taste of Vermont’s culinary delights or simply looking for a comfortable spot to enjoy a delicious meal, The Worthy Kitchen in Woodstock promises an unforgettable dining experience that captures the essence of Vermont’s culinary heritage and community-focused spirit.

16. Shop locally made Andrew Pearce Bowls

The Andrew Pearce Bowls store in Vermont is a captivating destination for admirers of handcrafted wooden artistry. Located just outside of the western border of Woodstock, this family-owned business has been creating exquisite wooden bowls for many years. The store was created by Andrew Pearce. Andrew’s brother, Simon, runs Simon Pearce Glass, and his other brother, Stephen, runs Shanagarry Potters. Needless to say, being a craftsman runs in the Pearce family.

As visitors step into the store, they are greeted with an array of stunning hand-turned wooden bowls, each crafted with meticulous attention to detail and a deep respect for the natural beauty of the wood. The store’s warm and inviting ambiance invites guests to explore the craftsmanship and creativity that goes into each unique piece. From classic salad bowls to intricately designed serving platters, the Andrew Pearce Bowls store offers a range of sizes and styles that cater to every taste and purpose. Beyond the bowls, visitors can also learn about the craftsmanship process, from the selection of sustainably sourced wood to the delicate turning and finishing techniques. 

Whether you’re a collector of wooden art or simply appreciate the beauty of finely crafted objects, a visit to the Andrew Pearce Bowls store is a captivating experience that celebrates the artistry and dedication of Vermont’s artisan community.

17. Photograph the iconic Lincoln Covered Bridge

Photo by @tomriley on Instagram

The Lincoln Covered Bridge is a historical treasure that stands as a testament to the enduring charm of New England’s covered bridges. Originally built in 1877, this iconic bridge spans across the Ottauquechee River and is a beloved symbol of Vermont’s heritage. With its classic natural exterior and Pratt truss design, the Lincoln Covered Bridge exudes a sense of timeless elegance that captures the imagination of visitors. 

As one of the few remaining Pratt truss bridges in the state, it offers a unique opportunity to step back in time and experience the simplicity and craftsmanship of the past. Visitors are welcome to drive through the bridge and also explore along the river bank. Whether you’re a history enthusiast, a photographer seeking a picturesque subject, or simply looking to immerse yourself in the tranquility of the surrounding nature, a visit to the Lincoln Covered Bridge is a must.

Learn more about the Lincoln Covered Bridge

18. Watch a performance or movie at the Woodstock Town Hall Theatre

The Woodstock Town Hall Theatre in Woodstock, Vermont, is a cherished cultural landmark that brings the community together through the magic of performing arts. Located in the heart of this charming New England town, the theater’s historic building exudes timeless elegance, adding to the allure of attending a performance. With its diverse lineup of events, including concerts, plays, film screenings, and other artistic productions, the Town Hall Theatre offers a rich and engaging cultural experience for residents and visitors alike. 

The theater’s intimate setting provides a close connection between performers and the audience, enhancing the overall experience for all attendees. Whether you’re a lover of the arts, seeking an entertaining evening out, or simply looking to immerse yourself in the vibrant cultural scene of Vermont, the Woodstock Town Hall Theatre promises an enriching and memorable experience that celebrates the power of creativity and the spirit of community.

19. Enjoy a one-of-a-kind farm-to-table dinner at Kelly Way Gardens

Kelly Way Gardens is a farm-to-table program that was developed from the ground up to provide the Woodstock Inn & Resort with an on-site holistic food source. They focus on rare and heritage varieties. With with over 200 varieties of vegetables, 50 varieties of herbs and edible flowers, 75 varieties of berries and orchard plantings, and, a mushroom glen, the chefs at the Woodstock Inn always have fresh foods to use and be inspired by. In addition, the farm grows 200 different types of cut flowers which are put on display in the inn. Master gardener Benjamin Pauly tends to the 3-acre garden, which is harvested daily and given to the culinary staff while still warm from the sun.

Visitors of the farm are also able to sign up for Red Barn Dinners which are located right on the farm and feature Master Gardener Benjamin Pauly and Resort Executive Chef Rhys Lewis. Learn more at https://www.woodstockinn.com/do/things-to-do/red-barn-dinners  

20. Drink like a local at Long Trail Brewing Company

Woodstock, Vermont is sadly not home to its own brewery. But luckily Long Trail Brewing Company can be found right over the western border of the town in Bridgewater. The Long Trail Brewing Company is a celebrated destination for beer enthusiasts and a testament to Vermont’s thriving craft beer culture. Established in 1989, the brewery takes its name from Vermont’s iconic Long Trail, a hiking trail that winds through the state’s stunning landscapes. The brewery’s location, surrounded by the Green Mountains, provides a scenic and inviting setting for visitors to savor their brews. 

Long Trail Brewing Company is known for its commitment to crafting high-quality, flavorful beers using locally sourced ingredients, including hops and malt. With a diverse selection of ales and lagers, the brewery offers something to suit every palate, from classic IPAs to rich stouts and refreshing wheat beers. In addition to the delectable brews, visitors can enjoy tours of the facility, gaining insight into the brewing process and the company’s dedication to sustainability. The brewery’s friendly and welcoming atmosphere, along with its passion for craftsmanship, make it a must-visit destination for beer aficionados seeking a taste of Vermont’s renowned craft beer scene.


As we conclude our exploration of Woodstock, Vermont, it becomes evident that this idyllic town is a destination that leaves a lasting impression on all who visit. Its timeless beauty, rich history, and warm hospitality make it a cherished gem among New England’s many treasures. Whether strolling through the charming downtown, admiring the iconic covered bridges, or reveling in the natural wonders that surround the town, Woodstock offers a delightful escape that captivates the senses and rekindles the spirit of adventure. 

From its picturesque landscapes to its vibrant cultural scene, Woodstock beckons travelers to slow down, savor the moment, and embrace the simple pleasures of life. So, whether you’re a history enthusiast, nature lover, or seeker of quaint delights, Woodstock, Vermont, promises an unforgettable journey filled with unforgettable memories that will stay with you long after you bid this enchanting town farewell.

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Tom Riley

Hi! I'm Tom. I am the creator of GoXplr. I started this website with a focus on helping people explore better and explore more. I am based in New England and obsessed with traveling. Here at GoXplr, you will find expert blog posts and also maps containing all of the best places to explore. These blogs and maps have taken thousands of hours to complete. I hope you enjoy this resource and it inspires you to get out and explore!

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