22 Best & Fun Things To Do in Woodstock, VT

Are you seeking fun, entertaining, and educational things to do to make your planned trip to Woodstock memorable? Your search is over! Join us as we dig deep into 22 fun and best things to do in Woodstock, Vermont, to get a fulfilled and special trip.

Woodstock, Vermont, is a charming and historic town nestled amidst the scenic beauty of Vermont. Known as the “quintessential Vermont village,” Woodstock offers a quintessential New England experience, rich in history and natural beauty.

Wander through the charming tree-lined streets, lined with colonial architecture, restored Georgian, Federal Style, and Greek Revival homes, and a covered bridge in the center of town. Explore the many art galleries, boutiques, bookstores, and local craft shops.

Explore the nearby Marsh-Billings-Rockefeller National Historical Park, hike or bike on scenic trails, or go for a swim or boat ride on the Ottauquechee River. In the winter, enjoy skiing, snowboarding, and other winter sports at nearby ski resorts.

Catch a performance at the renowned Woodstock Town Hall Theatre, or visit the Billings Farm & Museum to learn about Vermont’s agricultural history. The town also hosts a variety of festivals and events throughout the year, such as the Woodstock Summer Market and the Wassail Weekend.

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22 Best and Fun Things To Do In Woodstock, VT   (2024)

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1. Woodstock Town Historic District

Exploring the Woodstock Town Historic District is one of the most exciting things to do in Woodstock, Vermont. Established in 1995, the Woodstock Town Historic District is a charming and visually significant area that encompasses most of the historic center of the town.

The Woodstock Town Historic District reflects the town’s evolution over the centuries. The layout, with its central green and radiating streets, reflects early New England town planning. The architecture showcases the prosperity that Woodstock enjoyed during different periods. Walking through the district is like stepping back in time.

Explore the many shops and boutiques lining the streets. You’ll find a variety of offerings, from locally-made crafts and souvenirs to high-end clothing and home decor.

What’s more, the Woodstock Town Historic District invites you to immerse yourself in the local art scene by visiting the many galleries showcasing the works of Vermont artists. Delve deeper into Woodstock’s history by visiting the Woodstock Historical Society & Museum or the Billings Farm & Museum.

Address: 31 The Green, Woodstock, Vermont. , United States.

2. Woodstock Wassail Weekend

One of the most fun things to do in Woodstock, VT, in the winter is to explore Woodstock Wassail Weekend with your family. Woodstock Wassail Weekend is a festive holiday celebration held during the first weekend of December.

This cherished tradition is steeped in history and local charm, transforming the town into a winter wonderland. The town transforms with twinkling lights, festive decorations, and holiday cheer.

The carriage rides offer a magical way to experience the town, clopping through the snow-covered streets with festive lights twinkling overhead. Caroling fills the air, adding to the joyous atmosphere. You might even hear performances by local choirs or carolers.

The Billings Farm & Museum often joins the festivities, offering holiday decorations and special events related to Victorian Christmas traditions. You can also explore the town center, which is decorated for the holidays, and enjoy the festive ambiance. Many shops and businesses offer special sales and promotions during the weekend.

Address: Woodstock, Vermont, United States.

3. Woodstock Recreation Department

Exploring the Woodstock Recreation Department is one of the most fascinating things to do in Woodstock, VT, with your family.

The Woodstock Recreation Department strives to keep Woodstock residents and tourists active and entertained. This recreational park offers a variety of programs throughout the year for all ages.

This includes youth sports leagues, adult sports leagues, enrichment programs like arts and crafts or cooking classes, community events like festivals or movie nights, and senior programs focused on fitness or social gatherings.

Address: 54 River Street, Woodstock, VT 05091, United States.

4. Billings Farm & Museum

Visiting Billings Farm & Museum is one of the most interesting things to do in Woodstock, VT, with your family. Billings Farm & Museum is an award-winning destination that blends a fully-operating Jersey dairy farm with educational exhibits and interactive programs.

This historic site, regarded as one of the finest outdoor history museums in the country, offers a unique opportunity to learn about Vermont’s agricultural heritage and experience farm life firsthand.

Visitors can explore meticulously restored barns and farmhouses, witnessing the evolution of farm operations throughout the 19th century.

In addition, this farm offers daily programs and demonstrations showcasing farm chores, animal husbandry, and traditional cheesemaking techniques using Billings Farm’s herd of prize-winning Jersey cows.

The museum also features educational exhibits that showcase Vermont’s agricultural history and the importance of sustainable farming practices.

Address: 69 Old River Road, Woodstock, VT 05091, United States.

5. F.H. Gillingham & Co.

Established in 1886, exploring F.H. Gillingham & Co. is one of the most exciting things to do in Woodstock with your family.

F.H. Gillingham & Co. is the oldest, same-family-operated general store in the state, offering a unique blend of nostalgia and everyday essentials. Step inside and browse shelves brimming with Vermont-made maple syrup, cheddar cheese, and local crafts.

You’ll also find hardware, housewares, clothing, toys, and even fresh local produce in season. F.H. Gillingham & Sons is a must-visit for anyone seeking a taste of Vermont’s charm and a piece of Woodstock’s history.

Address: 16 Elm Street, Woodstock, Vermont 05091, United States.

6. The Principal Public House

Craving a pub experience with a touch of class? Head to the Principal Public House in Woodstock, Vermont. This gastropub offers a step above the ordinary, serving elevated takes on classic pub fare.

One exciting point is that the Principal Public House offers juicy burgers made with premium beef, creative twists on fish and chips, and options for vegetarians and gluten-free diners. Complement your meal with a craft beer, choosing from local Vermont selections alongside other notable picks.

The Principal Public House provides a warm and inviting atmosphere, perfect for a casual gathering with friends or a relaxed evening out. On your visit to Woodstock, ensure to include The Principal Public House as one of the things to do in Woodstock, VT. 

Address: 24 Elm Street, Woodstock, VT 05091, United States.

7.  Woodstock Historical Society & Museum

Are you looking for fascinating things to do in Woodstock, VT, this weekend? Then you should explore the Woodstock Historical Society & Museum with your family.

Situated in the heart of town at the historic Eames House, the museum offers a collection of artifacts, exhibits, and programs that bring Woodstock’s past to life.

Discover stories about Woodstock’s transformation from a rural agricultural center to a thriving tourist destination. Admire paintings, photographs, documents, textiles, and other artifacts that tell the story of the people, places, and events that shaped Woodstock.

The museum also hosts special events and programs throughout the year, offering lectures, workshops, and family-friendly activities.

Address: 26 Elm Street, Woodstock, VT 05091, United States.

8.  Smith Memorial Library

Exploring the Smith Memorial Library in Woodstock, Vermont, is one of the most exciting things to do in Woodstock, Vermont, for book lovers. The Smith Memorial Library is a treasure trove of resources for the community.

Their extensive collection includes books, periodicals, and audiovisual materials for all ages, from classic novels to children’s favorites. They also offer a wealth of digital resources like ebooks, audiobooks, and online databases, accessible with a library card.

Beyond books, the library hosts programs and services like story time, author talks, computer classes, and local history events. It’s a true community hub, offering a welcoming space to read, learn, and connect.

Address: 10 The Grn. Woodstock, VT 05091, USA

9. Zest Woodstock

Spruce up your wardrobe and home at Zest Woodstock, a vibrant shop brimming with style. This local gem offers a curated selection of women’s clothing, catering to various tastes.

Whether you seek trendy pieces, timeless staples, or comfy everyday wear, Zest has something for you. They also boast unique jewelry that adds a personal touch to any outfit.

Beyond fashion, Zest features charming home decor accents. Find decorative objects, textiles, and other treasures to personalize your living space. Zest Woodstock is a delightful spot to discover unique finds while supporting local Vermont artisans and designers.

Your visit to Woodstock is incomplete without including Zest Woodstock as part of your things to do in Woodstock, Vermont.

Address: Woodstock, Vermont, United States.

10.  Woodstock Town Hall Theatre

One of the most interesting things to do in Woodstock, VT, at night is to explore the Woodstock Town Hall Theatre.

Built in 1900, it has transformed from the grand Woodstock Opera House into a vibrant cultural hub under the Pentangle Arts Council’s care. This beautiful neoclassical theatre boasts 390 seats and exceptional natural acoustics, making it an ideal venue for a diverse range of performances.

Woodstock Town Hall Theatre offers live music by local, regional, and national artists, theatrical productions ranging from classic plays to modern works, captivating dance performances, and even screenings of first-run and independent films.

The Woodstock Town Hall Theatre is not just a stage, it’s the heart of Woodstock’s cultural scene, fostering local artists, bringing renowned performers to town, and offering a space for the community to connect through the arts.

Address: 31 The Green 2, Woodstock, VT 05091, United States.

11. Mountain Meadows Thrift Shop

Visiting Mountain Meadows Thrift Shop is one of the most romantic things to do in Woodstock, VT, this weekend with your partner.

Unveiling pre-loved treasures is what thrift shops are all about, and a Woodstock shop could be your treasure trove.

Imagine browsing racks of gently used clothing and accessories for the whole family or scoring unique home goods like furniture, lamps, or quirky knick-knacks. You might even unearth hidden gems like books, games, or dishes at a fraction of their original cost.

Beyond the thrill of the hunt, shopping at a thrift shop benefits the community. Proceeds often support local charities or social causes, and by choosing pre-loved items, you contribute to a more sustainable lifestyle.

So, if you’re looking for something unique, budget-friendly shopping, and a chance to do good, a Woodstock thrift shop is worth exploring.

Address: Woodstock, Vermont, United States.

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Are you exploring other attractions in Vermont? Why not check out some fun things to do in Rutland, fun things to do in Killington, and fun things to do in Brattleboro?

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12. Magic Hat Brewery

Located in Burlington, Vermont, exploring Magic Hat Brewery is one of the fun things to do near Woodstock, VT, for beer enthusiasts. This brewery offers a vast selection of craft beers on tap, with unique flavors and local ingredients.

Magic Hat Brewery specializes in certain styles and offers a range to please every palate. The atmosphere is typically casual and inviting, with some breweries featuring outdoor seating for sunny days.

Beyond the beer, Magic Hat Brewery is a community hub where you can enjoy delicious pub fare or food truck options alongside your brew. This brewery hosts events like live music or trivia nights, making it a fun place to socialize and support local businesses.

Address: 431 Pine Street, Burlington, VT, United States.

13. Woodstock Gallery

Unveiling a treasure trove in Woodstock Gallery is one of the most fun things to do in Woodstock, VT, for art enthusiasts.

The Woodstock Gallery is a must-visit attraction that celebrates diversity, showcasing a range of artistic styles.

Whether you’re drawn to captivating paintings, intricate sculptures, or eye-catching jewelry, you’re sure to find something that sparks your interest. The gallery prioritizes high-quality pieces, ensuring a delightful experience for every visitor.

Beyond the art itself, the Woodstock Gallery fosters a welcoming atmosphere. Explore at your own pace, ask questions of the knowledgeable staff, and potentially discover a new favorite artist.

By visiting, you’re not just admiring art; you’re supporting the creative endeavors of local and regional talents. So, if you’re searching for exceptional artwork and a chance to connect with the local art scene, The Woodstock Gallery awaits.

Address: 6 Elm Street, Woodstock, VT 05091, United States

14. The Spa at the Woodstock Inn & Resort

Are you looking for a place to relax on your own and be taken care of? Look no further; the Spa at the Woodstock Inn & Resort is just the best place for you.

The Spa at the Woodstock Inn & Resort at Woodstock boasts a variety of treatment rooms, including couples’ rooms, a hydrotherapy room, and a relaxation lounge.

With a wide range of treatments available, from massages and facials to body wraps and scrubs, there’s something for everyone at The Spa at the Woodstock Inn. This spa also offers seasonal and signature treatments that are unique to The Woodstock Inn & Resort.

The staff at The Spa at the Woodstock Inn & Resort are all highly trained and experienced in providing a variety of spa services. Enjoy a calming and relaxing atmosphere, perfect for unwinding and de-stressing.

Address: 14 The Green, Woodstock, VT 05091, United States.

15. Marsh-Billings-Rockefeller National Historical Park

Exploring Marsh-Billings-Rockefeller National Historical Park is one of the most exciting things to do in Woodstock, Vermont, with your family.

Marsh-Billings-Rockefeller National Historical Park is Vermont’s only national park and a great place to learn about conservation history and the evolving nature of land stewardship in America.

Built in 1807 by George Perkins Marsh, the mansion is a beautiful example of Federal-style architecture. Tours are available of the mansion, which offer a glimpse into the lives of the Marsh, Billings, and Rockefeller families.

One outstanding feature of Marsh-Billings-Rockefeller National Historical Park is that this park’s forest is one of the oldest scientifically managed forests in the country. Visitors can hike or bike on the park’s many trails and learn about the history of forestry in Vermont.

Address: 69 Old River Road, Woodstock, VT 05091, United States.

16.  Mount Tom

One of the most interesting places to visit in Woodstock, VT, is Mount Tom. Standing at 1,357 feet, Mount Tom offers numerous opportunities for outdoor recreation.

Situated in the northeastern part of Woodstock, Vermont, this attraction is flanked by Vermont Route 12 and Prosper Road. There are multiple hiking, running, and Nordic skiing trails leading to the peak. The Pogue and Mount Tom Trail is a popular 4.2-mile loop trail that offers scenic views of the forest and surrounding areas.

The trails up Mount Tom are generally easy to moderate. The final ascent to the peak can be a bit steeper and may require the use of a guide wire in some sections.

Address: 69 Old River Road, Woodstock, VT 05091, United States.

17. Saskadena Six

One of the best things to do in Woodstock, VT, for skiers is to explore the Saskadena Six. The resort was originally called Suicide Six and was renamed Saskadena Six in 2022.

Saskadena Six is famous for its gentle slopes and easy-riding terrain, making it perfect for families and beginners. There are 23 trails serviced by 3 lifts. In addition to winter sports, Saskadena Six offers over 6 miles of mountain bike trails for visitors to enjoy during the summer months.

The resort hosts the longest-running ski race in North America, the Fisk Trophy Race. It was first held in 1937 and is a rite of passage for serious eastern ski racers.

Address: 247 Stage Road, South Pomfret, Vermont 05067, United States.

18. Ottauquechee River

Immersing yourself in the serenity of the Ottauquechee River is one of the free things to do in Woodstock, VT. The river flow is a 41.4-mile-long tributary of the Connecticut River, winding its way through eastern Vermont.

This river is home to a variety of fish species, including trout, bass, and pickerel. The calm waters of the Ottauquechee River are perfect for paddling enthusiasts. On a hot summer day, you can take a dip in the refreshing waters of the river.

The Ottauquechee River Trail is a 3-mile family-friendly path that follows the riverbank. It offers beautiful views of the river, fields, woodlands, and even mountains.

Address: Woodstock, VT 05091, United States.

19. Quechee State Park

One of the most thrilling things to do in Woodstock, VT, is to visit Quechee State Park with your kids. Visitors can look down at the Ottauquechee River, flowing 165 feet below viewing points along Route 4.

This park has 45 tent and trailer sites and 7 lean-to sites. It also features restrooms with flush toilets, hot and cold running water, and coin-operated showers available for campers.

Quechee State Park features several hiking trails in the park, including a trail along the gorge that offers stunning views of the Ottauquechee River, which is also a great spot for swimming.

What’s more, this park has several picnic areas, including one with a pit toilet located next to the gorge. Quechee State Park is home to a variety of wildlife, including deer, fox, and beaver. Cross-country skiing is a popular activity in the park during the winter months.

Address: 5800 Woodstock Road, Hartford, VT 05047, United States.

20. The Red Rooster

Are you searching for one of the best places to enjoy a yummy meal? Look no further; The Red Rooster has got you covered. This restaurant offers a comfortable and upscale dining experience.

The restaurant has a sophisticated yet inviting atmosphere, perfect for a special occasion or a relaxing evening out. The Red Rooster features a modern interpretation of American classics. This restaurant also showcases fresh, seasonal ingredients sourced from Vermont purveyors.

The menu offers a wide range of dishes, including steaks, seafood, pasta, and vegetarian options. Take some time off in Woodstock, Vermont, and enjoy a good meal at The Red Rooster.

Address: 14 The Green, Woodstock, VT 05091, United States.

21. Sugarbush Farm

One of the most fascinating things to do near Woodstock, VT, with your family is to visit Sugarbush Farm.

The Sugarbush Farm is a family-run farm located a few miles outside of Woodstock, Vermont. They are famous for their excellent waxed cheeses and pure Vermont maple syrup, both made right on the farm.

Learn about the process of making maple syrup, from tapping the trees to boiling down the sap. Check out 15 varieties of Sugarbush Farm’s award-winning cheeses, including the Original Naturally Smoked Cheddar and the 6-Year Aged Cheddar.

In addition, take a walk in the woods and see how maple trees are tapped. During the warmer months, you can interact with the farm animals, including cows, sheep, and goats.

Enjoy a picnic lunch in the scenic Vermont countryside. Purchase cheese, maple syrup, and other Vermont products to take home with you.

Address: 591 Sugarbush Farm Road, Woodstock, VT 05091, United States.

22. Central Street Yoga & Meditation

One of the many mind-clearing things to do in Woodstock, VT, is to take a timeout and visit Central Street Yoga & Meditation.

This studio specializes in Svaroopa® yoga, a gentle and restorative practice that focuses on core release and unwinding deep spinal tension.

What’s more, it also offers yoga therapy, which has great benefits for your soul and mind. On your visit to Woodstock, VT, ensure to spend some quality time at Central Street Yoga & Meditation.

Address: 59 Central Street, Woodstock, VT 05091, United States.

Plan Your Trip To Woodstock, VT

Woodstock, Vermont, offers many thrilling opportunities to discover and embark on, from the exciting Quechee State Park to the peaks of its scenic vistas.

If you’re planning a visit, this amazing town promises memories that will linger long after the trip has concluded. We hope this guide serves as a comprehensive starting point on your journey of discovery and wonder. Safe travels!