21 Fun Things To Do In Woodstock (VT)

The charming town of Woodstock in Vermont was voted the “Prettiest Town in America.”

It offers several unique attractions such as beautiful architecture, world-class farms, and great restaurants.

It’s also a great place to experience the state’s other interests, such as Vermont Hospitality.

Woodstock continues celebrating its American charm as a town dedicated to its heritage in tourism and artisan culture.

It also offers several outdoor recreation activities and shopping. The article covers some exciting Things To Do In Woodstock (VT).

Where Is Woodstock, Vermont?

The town of Woodstock is the county seat of Windsor County, Vermont. According to the census of 2020, the town’s population was 3,005.

It includes the villages of South Woodstock, West Woodstock, and Taftsville.

According to the US Census Bureau, the town has an area of 44.6 square miles. It has a land area of 44.4 square miles and a water area of 0.27 square miles.

The Ottauquechee River passes through the town. It’s about 250 miles from New York City and is a three-hour drive from Boston.

It can be reached via plane through Lebanon Airport or by car.

Things To Do In Woodstock (VT)

Despite its small size, Woodstock still has plenty of things to keep its residents busy.

Besides the natural attractions, such as forests and farmland, the town also offers various other recreational activities.

In this article, we will discuss some of the best things to do in Woodstock, Vermont, and advise where and what to do in the town. These are some of the things to do in Woodstock, Vermont;

1. Woodstock Central Street and The Green

The heart of Woodstock is The Green and Central Street. This area is filled with restaurants, cafes, and independent boutiques.

These areas are known for their unique offerings.

Address: The Green and Central Street is located in Woodstock, VT 05091, United States.

2. Woodstock History Center

One of the first things to do in Woodstock is to visit the town’s museum. This facility is dedicated to preserving the history of the city.

It features various exhibits that tell the story of the people who lived in the area.

The museum’s exhibits include multiple artifacts such as paintings, books, and photographs.

It’s a must-visit for anyone interested in learning more about the town.

Address: It is located at 26 Elm St, Woodstock, VT 05091, United States.

3. Woodstock Middle Covered Bridge

Photo by James Walsh via Flickr

Many people in New England and Vermont know the region’s covered bridges.

These structures, constructed during the 19th century, are considered to be some of the most significant architectural landmarks in the area.

The bridges were constructed to withstand the effects of heavy snowfalls and prevent flooding.

These bridges also provided safe shelters for people who were caught in storms.

They additionally helped local farmers by making it easier for them to move their livestock.

Due to the popularity of these structures, they have become significant tourist attractions in the area.

One of these is the Woodstock Middle Covered Bridge, which spans the river and is considered one of the region’s most beautiful bridges.

Although the bridge was only constructed in 1969, it looks ancient because its engineers used traditional methods to replace its original structure.

This bridge also has a separate walkway for passengers. This is one of the most exciting things to do in Woodstock, Vermont.

Address: It is situated at Mountain Ave, Woodstock, VT 05091, United States.

4. Woodstock Farmers Market

One of the town’s most popular attractions is the Woodstock Farmers Market, located about a mile from the city. It’s open every Tuesday through Sunday.

The market features several food products, including fresh fruits and vegetables, dairy, and eggs.

It also sells various specialty pantry items and sandwiches. All food products sold at the market are made from local ingredients.

The market opens at 9 am and is a great place to pick up essential supplies before heading out on a day trip.

Address: This farmers market is located at 979 W Woodstock Rd, Woodstock, VT 05091, United States.

5. Sleepy Hollow Farm

Photo by Matt Shalvatis via Flickr

Another popular attraction in Woodstock is the Sleepy Hollow Farm.

This farm is located outside the town and features a variety of outhouses and barns. This property is set in a beautiful area of Vermont.

The farm is about 15 minutes away from the town on Cloudland Road.

It’s a great place to take a break from the hustle and bustle of the city and explore the countryside.

Address: Sleepy Hollow Farm is at 3429 Cloudland Rd South, Woodstock, VT 05091, United States.

6. Sugarbush Farm

Photo by Matthew D. Britt via Flickr

Another great place to visit in the area is Sugarbush Farms, which is a 500-acre farm that a local family owns.

This property is known for its maple syrup and cheese production.

The farm’s owners, the Luce family, welcome visitors and encourage them to explore the property.

They also provide tours and allow people to taste their syrups and cheese.

In addition, workshops are open to enable people to learn more about making these products.

Address: Sugarbush Farm is located at 591 Sugarbush Farm Rd, Woodstock, VT 05091, United States.

7. Jenne Road Farm

Photo by Jitze Couperus via Flickr

The other farm popular in the area is the Jenne Road Farm, which features barns and outhouses painted in vibrant colors. This working farm has been in operation for the past two decades.

Unfortunately, it’s impossible to visit the farm and take a complete look at its various structures. However, you can still stop by and pick up some maple syrup or take a quick picture.

Address: Jenne Road Farm is at 1279-1163, Jenne Rd, Reading, VT 05062, United States.

8. Billings Park and Mount Tom

If you’re looking for an area that’s close to the center of Woodstock and is famous for its hiking and outdoor activities, Mount Tom is a perfect choice.

This mountain peak is located in Billings Park. Various hiking trails and walking paths can be accessed through this complex.

One of the easiest ways to access Mount Tom is a 4-mile walk. This route has a noticeable elevation but is not too challenging for most people.

Reaching the summit of Mount Tom provides a spectacular view of the town of Woodstock.

This is certain during the fall season when the various forest colors will be seen.

Address: The Billings Park and Mount Tom is at 54 Elm Street, Woodstock, VT 05091, United States.

9. Billings Farm and Museum

The location of the farm and its proximity to the center of Woodstock make it an ideal choice for people looking to explore the area without a car. It also hosts events and educational programs.

The farm is also equipped with live demonstrations and exhibitions that will help people gain a deeper understanding of the agricultural practices in the area.

Address: Billings Farm and Museum is at 69 Old River Rd, Woodstock, VT 05091, United States.

10. Mount Peg

Another popular hiking destination in Woodstock is Mount Peg, located on the other side of the Ottauquechee River.

It offers a variety of activities and trails that can be accessed through this area.

The path you’ll follow through the woods and meadows before reaching Mount Peg has a thicket of vegetation and open fields. There are picnic tables and benches at the top of the mountain.

Like Mount Tom, this mountain peak offers a 360-degree view of the town of Woodstock.

It’s also an excellent choice for families with young children.

In addition, Mount Peg is accessible all year round, making it an ideal choice for people who are not afraid to try new activities.

Address: Mount Peg is at 12 Golf Avenue, right in the middle of Woodstock Village.

11. Quechee State Park

Photo by Jimmy Emerson, DVM via Flickr

Located 10 minutes from Woodstock, Quechee is a small town known for its state park. This park is also a great choice for people looking to explore the area.

Look at the Quechee gorge, carved during the last Ice Age and measures 165 feet deep. It’s also an excellent choice for people learning more about its history.

The gorge’s visitor center can additionally be visited to learn more about its history.

Quechee State Park is open from May to October. People planning on visiting Vermont during the fall should check the dates of the year when this area will open.

Address: The Quechee State Park is at 6800 Woodstock Rd, Hartford, VT 05047, United States.

12. Coolidge State Park

This park is also an excellent choice for people looking to explore the area. It’s located 12 miles southwest of Woodstock.

Like Quechee State Park, this facility is only open from May to October. The hiking trails in the park lead to various viewpoints.

This facility also offers dramatic views of the Green Mountains and the Black River Valley.

This is one of the best state parks in Vermont and is known for its campsites. This facility also has RV hook-ups.

Address: The Coolidge State Park is at 855 Coolidge State Park Rd, Plymouth, VT 05056, United States.

13. Enjoy the Local Cheese

The town of Woodstock is known for its cheese, and it’s an excellent choice for people who are looking to explore the area.

Several activities and events are available in this area related to cheese.

14. Enjoy some Ice Cream

All the ice creams in Vermont are made with local ingredients, such as maple syrup and walnuts.

It’s also possible to create your ice cream by adding various toppings such as cookies and crackers.

The location of the Mountain Creamery is around 10 minutes from the Village Green.

If you’re planning on visiting this area during your time, you might want to take a walk along the river.

This can take around 90 minutes, depending on your schedule.

Address: The Mountain Creamery is at West, 4, 4374 W Woodstock Rd, Woodstock, VT 05091, USA.

15. Taftsville Covered Bridge

Photo by Frank Kovalchek via Flickr

Visiting this bridge is one of the fun things to do in Woodstock, Vermont.

The Taftsville Covered Bridge was constructed in 1836 and is considered one of the oldest in New England.

If you’re planning on visiting this area, you might want to park near the bridge and walk down the river to see the waterfall.

Address: Taftsville Covered Bridge is in Woodstock, VT 05091, USA.

16. Long Tail Brewery

Long Tail Brewing Company was founded in 1989 and is located on the banks of the Otaguechee River. This facility provides a lovely setting to drink their beers.

The 273-mile hiking trail inspired the company’s name through the Green Mountains.

They brew different beers, such as India Pale Style (IPAs). They also create seasonal blends.

Address: The Long Tail brewery is at 5520 US-4, Bridgewater, VT 05035, United States.

17. Harpoon Brewery Taproom and Beer Garden

The Harpoon Brewery is located on the Connecticut River’s side and overlooks New Hampshire.

This facility features a large beer garden ideal for enjoying their various beers.

Their woodfired pizzas are also known to be very good. Besides being able to brew their beer, this establishment additionally has a variety of heated cabins that are ideal for winter visitors.

Address: The Harpoon Brewery at 336 Ruth Carney Drive, Windsor, VT 05089, United States.

18. 506 On the River Inn Woodstock

This luxury base camp is located in Woodstock, Vermont, equipped with an indoor swimming pool and sauna.

All of its boutique rooms have private bathrooms and a balcony. Studio apartments come with a personal kitchen.

Address: The 506 On the River Inn is at 1653 W Woodstock Rd, Woodstock, VT 05091, United States.

19. The Shire Woodstock

The pet-friendly Comfort Inn is located on the banks of the Ottauquchee River.

All the guest rooms have been decorated with traditional furniture and situated on the river’s edge.

Address: The Shire Woodstock is at 46 Pleasant St, Woodstock, VT 05091, United States.

20. The Vesper Woodstock

The Vesper Woodstock is located near the Village Green. It features a variety of antiques and oriental rugs, as well as a private bathroom. The rooms are bright and cheerful.

Address: The Vesper Woodstock is at 21 Pleasant St, Woodstock, VT 05091, United States.

21. Morning Village Walk

You can begin your morning village walk at the Woodstock Pharmacy and end at the Mon Vert Cafe, where you can enjoy a coffee and a view of Vermont from the covered bridge.

This is one of the fun things to do in Woodstock, Vermont.

Best Time To Visit Woodstock, Vermont

Although Vermont is never out of season, it’s best to visit the state in May/June or September/October.

During these seasons, the weather is generally favorable, and plenty of activities keep you busy.

Cost Of Visiting Woodstock, Vermont

The average cost of a vacation in Woodstock is around $123 a day. This is based on the expenses other travelers have incurred during their stay in the area.

Some of the most common costs that past travelers have incurred during their time in the town were local transportation and meals.