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30 Things to Do in Woodstock, Vermont(VT)

Green Mountains, Woodstock, Vermont, is a quintessential New England town that offers a perfect blend of natural beauty, historic charm, and outdoor adventure. Whether you're drawn to its stunning landscapes, rich history, or vibrant cultural scene, Woodstock is an ideal destination for anyone looking to experience authentic Vermont life. From the winding streets of the village to the surrounding forests and mountains, there's always something to discover in this picturesque town.

Known for its cobblestone streets, 19th-century architecture, and proximity to hiking trails, Woodstock is a place where both history and nature seamlessly coexist. While visiting, you can also explore nearby attractions, including things to do in Killington, Vermont, which offer a perfect blend of outdoor adventure and stunning mountain views.

Infographic - 30 Things to Do in Woodstock, Vermont

30 Things to Do in Woodstock, Vermont

Woodstock, Vermont, is known for its charming atmosphere, beautiful landscapes, and rich history. Whether you’re looking for outdoor adventures, historical landmarks, or local shopping, this small town offers something for everyone, while just a short drive away, there are also many exciting things to do in Manchester, Vermont (VT). Here’s a list of top activities to enjoy when visiting Woodstock:

1. Visit Billings Farm & Museum

Short Description: Billings Farm & Museum is a working dairy farm that provides visitors with a hands-on experience of Vermont’s rural life. The museum offers exhibits on agriculture, farming history, and features live farm animals.

Pros:

  • Family-friendly experience

  • Learn about Vermont’s agricultural history

  • Interactive exhibits with animals

  • Beautiful farm setting

Cons:

  • Limited activities during off-seasons

  • Can be crowded on weekends

Key Attractions and Events:

  • Historic farm buildings and exhibits

  • Live animal interactions

  • Seasonal events like Maple Sugar Fest and Harvest Festival

2. Explore Marsh-Billings-Rockefeller National Historical Park

Short Description: This park offers a scenic escape with its well-preserved forests, hiking trails, and historic homes. It showcases the connection between conservation, nature, and history.

Pros:

  • Excellent for hiking and nature walks

  • Rich in history and educational value

  • Beautiful natural surroundings

Cons:

  • Can be difficult to access during winter months

  • Limited facilities on the trails

Key Attractions and Events:

  • Mansion tours showcasing conservation history

  • Wildflower walks in the spring

  • Scenic drives with views of the park

3. Stroll through Woodstock Village Green

Short Description: Woodstock Village Green is a picturesque park located in the heart of Woodstock. Surrounded by historic buildings, it’s a perfect spot to relax, enjoy the outdoors, and take in the quaint atmosphere, while also being a short drive from plenty of things to do in Burlington, Vermont (VT).

Pros:

  • Central location with easy access to local shops

  • Ideal for a leisurely walk or picnic

  • Great spot for photography

Cons:

  • Can get crowded during peak tourist season

  • Limited seating options in busy times

Key Attractions and Events:

  • Farmers’ market on Saturdays

  • Annual town events and festivals

  • Historic buildings and town square

4. Browse F.H. Gillingham & Sons General Store

Short Description: F.H. Gillingham & Sons is a historic general store that’s been a staple of Woodstock for over a century. It offers a wide selection of local products, crafts, and unique gifts.

Pros:

  • Charming historic atmosphere

  • A great place for souvenirs

  • Offers locally sourced goods

Cons:

  • Can be a bit pricey for certain items

  • Limited selection during off-seasons

Key Attractions and Events:

  • Local Vermont goods like maple syrup and cheese

  • Seasonal product selections

  • Friendly and knowledgeable staff

5. Photograph Middle Covered Bridge

Short Description: The Middle Covered Bridge is one of Woodstock’s iconic landmarks. This beautifully preserved bridge is a great spot for photography, particularly in the fall when the surrounding foliage is at its peak.

Pros:

  • Ideal for photographers, especially during fall

  • Historic charm and beauty

  • Picturesque setting by the river

Cons:

  • Small area around the bridge

  • Difficult parking during peak seasons

Key Attractions and Events:

  • Scenic photo opportunities

  • Excellent autumn views

  • Historic covered bridge experience

6. Hike Mount Tom Trail

Short Description: The Mount Tom Trail offers a moderate hike with rewarding views of the town of Woodstock and the surrounding area. It’s perfect for those looking to enjoy the outdoors and experience a bit of Vermont’s wilderness.

Pros:

  • Moderate difficulty, suitable for most fitness levels

  • Spectacular views from the summit

  • Accessible year-round

Cons:

  • Can be muddy or slippery during rain

  • Limited facilities on the trail

Key Attractions and Events:

  • Panoramic views of Woodstock and the Green Mountains

  • Seasonal wildflower displays

  • Peaceful environment away from crowds

7. Enjoy Views from the South Peak Lookout

Short Description: The South Peak Lookout offers a breathtaking panoramic view of the Green Mountains and the town of Woodstock. This spot is ideal for nature lovers and those seeking a serene escape.

Pros:

  • Stunning views, especially at sunrise and sunset

  • Peaceful and quiet location

  • Ideal for picnics and relaxation

Cons:

  • Access may require a hike or drive up a steep road

  • Limited facilities at the lookout point

Key Attractions and Events:

  • Scenic views of the Green Mountains

  • Great for photography, particularly at golden hour

  • Hiking opportunities nearby

8. Visit the Norman Williams Public Library

Short Description: The Norman Williams Public Library is a charming and historic library located in downtown Woodstock. It offers a variety of books, programs, and a quiet space to relax or read.

Pros:

  • Quiet, peaceful atmosphere for reading or study

  • Historic architecture and design

  • Frequent community events and programs

Cons:

  • Limited hours on certain days

  • Small size compared to larger city libraries

Key Attractions and Events:

  • Local author readings and events

  • Community outreach programs

  • Free public access to books and materials

9. Explore Local Art at Collective—The Art of Craft

Short Description: Collective—The Art of Craft showcases local Vermont artists and artisans. The gallery features a diverse range of handcrafted art, from pottery to jewelry to textiles.

Pros:

  • Support local artisans and the craft community

  • Beautiful and unique artwork

  • A great place for finding one-of-a-kind gifts

Cons:

  • Artwork can be expensive

  • Limited availability of certain pieces

Key Attractions and Events:

  • Exhibits featuring local Vermont artists

  • Workshops and craft demonstrations

  • Opportunities to meet the artists

10. Tour the Woodstock History Center

Short Description: The Woodstock History Center is a museum that offers an in-depth look at the town’s history. From its colonial beginnings to modern times, it’s a must-visit for history buffs.

Pros:

  • Great for learning about Woodstock’s history

  • Family-friendly exhibits and activities

  • Well-curated historical displays

Cons:

  • Limited hours during the off-season

  • Smaller museum, can feel a bit cramped

Key Attractions and Events:

  • Artifacts from Woodstock’s early history

  • Special exhibits on local history

  • Historical walking tours available

11. Sample Cheese at Sugarbush Farm

Short Description:
Sugarbush Farm is a family-owned farm offering artisanal cheese, maple syrup, and a beautiful Vermont experience. You can sample a variety of delicious cheeses while enjoying the scenic views of the farm.

Pros:

  • Tasty selection of handcrafted cheeses and maple products.

  • Gorgeous views of the Green Mountains.

  • Friendly and informative staff.

Cons:

  • Limited hours during off-peak seasons.

  • Small farm with limited facilities.

Key Attractions and Events:

  • Cheese-making demonstrations (seasonal).

  • Maple syrup production tours in the spring.

12. Walk the Ottauquechee River Trail

Short Description:
The Ottauquechee River Trail offers a beautiful and relaxing walk along the river, with easy access from downtown Woodstock. It’s perfect for nature lovers who want a peaceful outdoor experience.

Pros:

  • Scenic and peaceful atmosphere.

  • Family-friendly with minimal difficulty.

  • Great for birdwatching and photography.

Cons:

  • Trail can be muddy after rain.

  • Limited shade, so it can be hot during summer.

Key Attractions and Events:

  • Gorgeous riverside views, especially in the fall.

  • Ideal for a short hike or leisurely walk.

13. Dine at The Prince & The Pauper Restaurant

Short Description:
The Prince & The Pauper is one of Woodstock’s finest dining establishments, offering an intimate atmosphere and a menu full of fresh, local ingredients. Whether you're celebrating a special occasion or just enjoying a quiet meal, this restaurant is a standout.

Pros:

  • Exquisite food with a seasonal menu.

  • Elegant setting perfect for romantic dinners.

  • Excellent wine list and attentive service.

Cons:

  • Can be pricey for some diners.

  • Reservations recommended as it gets busy.

Key Attractions and Events:

  • Special holiday menus.

  • Locally sourced Vermont dishes.

14. Sip Craft Beers at Long Trail Brewing Company

Short Description:
Long Trail Brewing Company is a local favorite for craft beer enthusiasts. Located just outside of Woodstock, it offers a variety of handcrafted beers with unique flavors and a welcoming atmosphere.

Pros:

  • Great variety of local craft beers.

  • Friendly and laid-back tasting room.

  • Outdoor seating with views of the brewery.

Cons:

  • Limited food options at the brewery itself.

  • Can get crowded during peak hours.

Key Attractions and Events:

  • Seasonal beer releases.

  • Brewery tours and events.

15. Explore Faulkner Park

Short Description:
Faulkner Park is a lovely spot to enjoy the outdoors in Woodstock. The park is known for its beautiful walking paths, open fields, and playgrounds, making it an excellent destination for families.

Pros:

  • Spacious park with plenty of room for picnics and outdoor games.

  • Peaceful setting perfect for a relaxing afternoon.

  • Dog-friendly.

Cons:

  • Limited amenities, such as restrooms.

  • Can get busy on weekends.

Key Attractions and Events:

  • Summer concerts and community events.

  • Fall foliage views from the park.

16. Go Antiquing at Unicorn Antiques

Short Description:
Unicorn Antiques is a charming store in Woodstock, filled with a wide array of vintage items and unique antiques. It’s a perfect place for anyone looking to find a one-of-a-kind souvenir or a special treasure.

Pros:

  • Wide selection of antiques and collectibles.

  • Friendly and knowledgeable staff.

  • Great for those who love vintage shopping.

Cons:

  • Prices may be higher than expected for some items.

  • Not ideal for those looking for modern products.

Key Attractions and Events:

  • Antique fairs and events held seasonally.

  • Special deals on select items during the holiday season.

17. Drive Along Scenic Route 4

Short Description:
Scenic Route 4 is one of the most picturesque drives in Vermont. As you drive along this winding road, you’ll be treated to breathtaking views of mountains, rivers, and quaint villages.

Pros:

  • Stunning views of the Vermont countryside.

  • Ideal for photography enthusiasts.

  • Perfect for a leisurely road trip.

Cons:

  • Can be tricky to navigate during winter months.

  • Some parts of the road can be narrow.

Key Attractions and Events:

  • Gorgeous views of the Green Mountains and Ottauquechee River.

  • Opportunity to stop and explore various small towns along the way.

18. Take a Horse-Drawn Carriage Ride in Winter

Short Description:
During the winter months, Woodstock offers a magical experience of a horse-drawn carriage ride. It’s a wonderful way to explore the snowy streets of the village and enjoy the winter scenery.

Pros:

  • Romantic and nostalgic experience.

  • Great for families and couples.

  • Beautiful views of the village in winter.

Cons:

  • Only available during the winter season.

  • Can be expensive for larger groups.

Key Attractions and Events:

  • Winter holiday events and decorations around Woodstock.

  • Christmas Eve carriage rides in the village.

19. Attend the Woodstock Wassail Weekend (December)

Short Description:
The Woodstock Wassail Weekend is a popular December event that celebrates the holiday season with festive activities like parades, carol singing, and horse-drawn sleigh rides. It’s one of the most anticipated events in the town.

Pros:

  • Fun for the whole family.

  • Vibrant and festive atmosphere.

  • Opportunity to experience traditional Vermont holiday celebrations.

Cons:

  • Can be crowded due to its popularity.

  • Limited accommodations in the area during this time.

Key Attractions and Events:

  • Holiday parades and horse-drawn carriage rides.

  • Artisan markets and local crafts.

20. Visit the Taftsville Covered Bridge

Short Description:
The Taftsville Covered Bridge is a beautiful and historic landmark just outside Woodstock. It’s one of Vermont’s most photographed covered bridges and offers a scenic spot for a peaceful visit.

Pros:

  • Rich history and charming architecture.

  • Great for photos, especially during fall or spring.

  • Quiet and peaceful location.

Cons:

  • Limited parking near the bridge.

  • Not much else to do nearby.

Key Attractions and Events:

  • Popular for photography, especially during the fall foliage season.

  • A part of Vermont’s rich covered bridge history.

21. Relax at The Spa at the Woodstock Inn

Short Description of Activity:
The Spa at the Woodstock Inn is the perfect place to unwind. This luxurious spa offers a variety of treatments, including massages, facials, and body wraps, all designed to relax and rejuvenate.

Pros and Cons:

  • Pros: Tranquil atmosphere, expert therapists, wide range of treatments, beautiful setting.

  • Cons: On the pricier side, reservations are required in advance.

Key Attractions and Events:
The spa uses organic products and features soothing treatments like the "Vermont Maple Sugar Body Scrub," perfect for those who want to experience a taste of the region while pampering themselves.

22. Bike the Woodstock Country Roads

Short Description of Activity:
Woodstock is surrounded by beautiful countryside, and biking the local roads is a fantastic way to explore the area. The country roads wind through charming villages, farmland, and scenic landscapes.

Pros and Cons:

  • Pros: Beautiful views, peaceful routes, ideal for all skill levels.

  • Cons: Can be challenging for beginners due to some hilly terrain.

Key Attractions and Events:
During the fall, biking the country roads allows you to enjoy the vibrant foliage. Many local bike rental shops in Woodstock offer guided tours or bike rentals.

23. Stop by the Farmers Market on Route 4

Short Description of Activity:
The Woodstock Farmers Market is a popular spot for locals and tourists alike. It’s a wonderful place to pick up fresh, locally grown produce, homemade goods, and artisanal products.

Pros and Cons:

  • Pros: Fresh and locally sourced food, friendly vendors, beautiful setting.

  • Cons: Market days may vary, and some items can be pricey.

Key Attractions and Events:
In addition to produce, you’ll find homemade baked goods, cheeses, and Vermont maple syrup. This is a great place to get souvenirs and taste the region’s specialties.

24. Try Maple Syrup Tasting at Local Sugarhouses

Short Description of Activity:
Vermont is famous for its maple syrup, and there’s no better place to experience it than at one of the many local sugarhouses. You can watch the syrup-making process and taste fresh, local maple syrup.

Pros and Cons:

  • Pros: Educational, delicious, family-friendly.

  • Cons: Seasonal activity (typically available in spring), limited to specific locations.

Key Attractions and Events:
Many sugarhouses offer tours during the sugaring season, showcasing the process from sap collection to syrup bottling. Don’t miss the chance to sample a variety of maple syrup!

25. Go Fly Fishing in the Ottauquechee River

Short Description of Activity:
The Ottauquechee River is renowned for its fly fishing opportunities. The calm waters and scenic surroundings make it a perfect spot for both beginners and seasoned anglers.

Pros and Cons:

  • Pros: Peaceful environment, great fishing conditions, beautiful landscape.

  • Cons: Requires a fishing license, and conditions may vary seasonally.

Key Attractions and Events:
The river is home to brown and rainbow trout. Fly fishing guides are available for those who want to improve their skills or get familiar with the area.

26. Visit the New England Falconry Experience

Short Description of Activity:
Get up close and personal with birds of prey at the New England Falconry experience. This unique adventure offers an introduction to the ancient art of falconry.

Pros and Cons:

  • Pros: Fascinating experience, interactive, educational.

  • Cons: Sessions can be short, limited availability, requires booking in advance.

Key Attractions and Events:
You’ll have the chance to hold and interact with birds like hawks and falcons, learning about their behavior and hunting techniques. It’s a must-visit for animal lovers and those interested in nature.

27. Picnic in East End Park

Short Description of Activity:
East End Park is a scenic location ideal for a relaxing picnic. With lush green spaces, a serene atmosphere, and the beautiful backdrop of the surrounding hills, it’s the perfect spot to unwind.

Pros and Cons:

  • Pros: Quiet, peaceful, family-friendly, accessible.

  • Cons: Limited facilities, may be crowded during peak season.

Key Attractions and Events:
The park features a well-maintained playground for children and beautiful walking paths. It’s also a popular spot for birdwatching, making it a great place to spend a leisurely afternoon.

28. Join a Yoga Class at the Blue Horse Inn

Short Description of Activity:
The Blue Horse Inn offers yoga classes for all levels in a relaxing, peaceful environment. The inn’s serene surroundings provide the perfect setting for practicing yoga.

Pros and Cons:

  • Pros: Stress-relieving, expert instructors, great for all skill levels.

  • Cons: Classes are limited, advanced reservations recommended.

Key Attractions and Events:
Yoga classes here are tailored to help you reconnect with nature and your inner self, often held in the tranquil environment of the inn’s spacious outdoor areas.

29. Experience Local Theater at Pentangle Arts

Short Description of Activity:
Pentangle Arts offers a variety of performances, from theater productions to live music and dance performances. It’s a great way to experience Woodstock's local arts scene.

Pros and Cons:

  • Pros: Variety of performances, high-quality productions, cozy venue.

  • Cons: Performance schedules may vary, tickets can sell out quickly.

Key Attractions and Events:
The theater often hosts seasonal events, with performances ranging from classic plays to contemporary works. Check their schedule for upcoming shows and performances.

30. Enjoy Fall Foliage on a Scenic Drive or Hike

Short Description of Activity:
Woodstock is one of the best places in New England to witness the spectacular fall foliage. Whether you choose to drive or hike, the colorful landscapes will leave you in awe.

Pros and Cons:

  • Pros: Stunning views, accessible to all ages, perfect for photography.

  • Cons: Only available during the fall season, can be crowded at peak times.

Key Attractions and Events:
Scenic drives and hiking trails through the Green Mountains offer breathtaking views of the vibrant fall colors. Popular routes include the Killington Scenic Drive and the Long Trail hike.

Unique Facts About Woodstock, Vermont

Historical Landmarks

Woodstock is home to a number of historic landmarks that reflect its rich past. One of the most iconic is the Woodstock Village Green, a charming park surrounded by beautiful historic buildings. Here, visitors can explore the Middle Bridge, an 1869 covered bridge that offers picturesque views of the Ottauquechee River. The Marsh-Billings-Rockefeller National Historical Park is another significant site, with its well-preserved mansion, gardens, and trails that tell the story of conservation and the Rockefeller family’s influence on the area.

Interesting Trivia About the Town

Woodstock is not just historically significant; it is also a town full of quirky facts. For instance, Billings Farm & Museum is one of the few remaining dairy farms that provides visitors with a glimpse of 19th-century farm life. The town is also famous for being the location of Vermont’s first-ever automobile accident, which occurred in 1898.

Moreover, Woodstock has earned the reputation of being a 'perfectly preserved' village, with much of its architecture dating back to the 19th century, which contributes to its historic charm.

Woodstock’s Cultural Significance

Woodstock plays a pivotal role in Vermont's cultural scene, being home to art galleries, museums, and cultural festivals. The Woodstock Arts Festival is one of the biggest events of the year, drawing artists, musicians, and visitors from all over the world. Additionally, Woodstock is home to a vibrant local music scene, with many venues offering live performances throughout the year. The Pentangle Arts organization is dedicated to bringing the arts to the community, with performances and exhibitions in dance, theater, and visual arts.

Best Time to Visit Woodstock, Vermont

Season Best Time to Visit Activities Available Weather Overview
Spring April - June Hiking, Art Events Mild temperatures
Summer July - August Festivals, Outdoor Dining Warm, pleasant
Fall September - November Fall Foliage, Tours Cool, crisp air
Winter December - March Skiing, Snowshoeing Cold, snowy

The best time to visit Woodstock depends on the activities you're most interested in. Spring and summer offer beautiful weather for outdoor activities like hiking, biking, and exploring the arts scene. Fall is perfect for those wanting to witness the spectacular foliage Vermont is known for, while winter provides the opportunity for skiing and other winter sports.

Unique Gems in Woodstock, Vermont

Hidden Spots and Off-the-Beaten-Path Places

While Woodstock’s main attractions are well-known, there are several hidden gems that offer a more intimate experience of the town. One such spot is Quechee Gorge, just a short drive from Woodstock. Known as Vermont’s “Little Grand Canyon,” it offers breathtaking views and is perfect for a scenic hike. Another hidden gem is the Vermont Marble Museum, where visitors can discover the history of Vermont’s marble industry and explore the impressive marble sculptures scattered throughout the museum.

Lesser-Known Local Favorites

For a true local experience, take a trip to The Woodstock Farmers’ Market. This quaint market is a favorite among locals, offering fresh produce, local cheeses, and handcrafted goods. It's a great place to sample Vermont's famous maple syrup and artisan products. Another lesser-known favorite is the Pond Village, a serene spot for those who want to escape the crowds and enjoy the quiet beauty of the area.

Must-See Scenic Views or Photo Ops

The views around Woodstock are nothing short of stunning. Mount Tom provides a relatively easy hike with incredible panoramic views of the town below, including the famed Middle Bridge and the surrounding countryside. Another scenic spot is the Ottauquechee River, where visitors can take in the reflection of the covered bridge and the surrounding hills, making for an unforgettable photo opportunity.

Day Itinerary in Woodstock, Vermont

If you're planning a short stay, here’s a suggested 1-2 day itinerary that covers the best of Woodstock:

Day 1: Explore the Village and Historic Landmarks

  • Morning: Start your day by strolling through the Woodstock Village Green. Visit the Woodstock Inn & Resort for breakfast, and take a walk through the historic Woodstock Covered Bridge.

  • Afternoon: Head to Billings Farm & Museum, where you can explore Vermont's agricultural history, and then take a scenic drive to Marsh-Billings-Rockefeller National Historical Park for a tour of the grounds.

  • Evening: Enjoy dinner at a local restaurant like The Prince & The Pauper or The Red Rooster. For dessert, stop by Sugarbush Farms to sample local cheeses and maple syrup.

Day 2: Outdoor Adventures and Scenic Views

  • Morning: After breakfast, embark on a hike at Mount Tom for a beautiful view of the surrounding landscape.

  • Afternoon: Head to Quechee Gorge for a quick visit, followed by a stop at the Vermont Marble Museum.

  • Evening: Wrap up your day with a relaxing dinner at The Wooden Spoon, known for its farm-to-table cuisine and cozy atmosphere.

How to Reach Woodstock, Vermont

Woodstock is easily accessible by car, train, or bus. The nearest major airport is Lebanon Municipal Airport (LEB) in New Hampshire, about 30 miles away. From there, visitors can rent a car and take a scenic drive to Woodstock.

If you're driving, Interstate 89 is the main route to reach Woodstock from major cities in Vermont and New Hampshire. Visitors can also take advantage of public transit options like Greyhound or Amtrak, which offer services to nearby towns.

For scenic drives, consider taking Route 12 from Windsor, which passes through rolling hills and offers a peaceful journey to Woodstock.

Conclusion

Woodstock, Vermont, is a destination that offers something for everyone—whether you’re a history buff, outdoor enthusiast, or art lover. From its charming village streets to the surrounding forests and mountains, Woodstock’s natural beauty and historic charm are truly unmatched. With something to do in every season, it’s no wonder that Woodstock is a must-visit destination in Vermont.

Whether you're visiting for a weekend getaway or a longer stay, you'll find plenty of activities to enjoy and memories to create. Don't miss the chance to explore this New England gem and discover all that Woodstock has to offer.

FAQs

What is the best time of year to visit Woodstock, Vermont?

The best time to visit Woodstock depends on your interests. Spring and summer are perfect for outdoor activities, while fall offers stunning foliage, and winter is ideal for skiing and snowshoeing.

What outdoor activities can you do in Woodstock?

Woodstock offers a variety of outdoor activities such as hiking, skiing, biking, and snowshoeing. You can also enjoy scenic drives and explore Vermont's natural beauty.

Are there any famous landmarks in Woodstock, Vermont?

Yes! Woodstock is home to historical landmarks like the Woodstock Covered Bridge, Billings Farm & Museum, and Marsh-Billings-Rockefeller National Historical Park.

What should I bring when visiting Woodstock in winter?

When visiting Woodstock in winter, be sure to pack warm clothing, including a winter coat, gloves, boots, and layers for outdoor activities like skiing and snowshoeing.

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