Woodstock, Vermont

Woodstock, VT Library
Woodstock, VT Library

Located in Windsor County, Vermont, to the west of Quechee along Route 4, Woodstock is comprised of 5 villages. These villages include the village of Woodstock, as well as the unincorporated villages of South Woodstock, West Woodstock, Taftsville and Prosper. The population of Woodstock,VT is approximately 3,000 people – nearly one third of which live in the village of Woodstock. The village of Woodstock took the nickname “Wireless Woodstock” because there is community wi-fi internet access that covers most of the village. The usage fee for the wi-fi, however, it is paid for through taxation.

Woodstock is home to a great walk-and-shop district, with many shops centered around the arts. The village is chock-full of restaurants and boutiques. Aside from shopping, there’s also plenty of recreational activities to be found in Woodstock. It’s a beautiful place to visit or live year round.

The Town of Woodstock, Vermont

History of Woodstock

Named after the town of Woodstock, in the County of Oxfordshire, England, Woodstock, Vermont was chartered in 1761 by NH Governor Benning Wentworth, through the New Hampshire Grants and was incorporated in 1837. First settled by James Sanderson and his family in 1786, Woodstock saw the construction of it’s first grist mill and sawmill in 1776 along the banks of the Ottauquechee River.

The town of Woodstock, like many other towns in the Upper Valley, has a wonderful and rich history of manufacturing and industry. Though development of the town was temporarily stunted by the Revolutionary War, post-war Woodstock developed quite quickly.

Soon after the Revolutionary War ended, factories started going up throughout town including a woolen factory, and factories that built horse saddles, luggage and leather goods, window sashes and blinds as well as factories that produced furniture, carriages and other goods and necessities.

The industrial revolution and the opening of the Woodstock Railroad in White River Junction, VT helped the town grow and thrive from the mid 1700s through the 1800s.

History Center - Woodstock, Vermont

Things to do in Woodstock, Vermont

There’s an amazing amount of things to do in the town of Woodstock. Whether you like exploring historical places or enjoy outdoor recreational activities, there’s something for everyone here.

Visit the Woodstock History Center to take a walk back in time. There you’l find a wonderful collection of antiques including toys, clothing and textiles, ceramics and silver, arts and period furniture. The building itself was constructed in 1807 for a village merchant by the name of Charles Dana. It was kept in the Dana family until 1943 until it was sold and subsequently turned into a museum. Visit, explore and ask about programs, classes and exhibitions that the Woodstock History Center offers.

Covered Bridges

Classic of the Upper Valley and New England as a whole, Woodstock is also home to covered bridges. The town has three covered bridges, the Middle Covered Bridge, the Taftsville Covered Bridge and the Lincoln Covered Bridge.

Middle Covered Bridge - Woodstock, Vermont
Middle Covered Bridge

The newest of the three is the Middle Covered Bridge, which is also known as the Union Street Covered Bridge. It was constructed in 1969, and rebuilt after an arson fire in 1974. It is an all-peg construction covered bridge. The bridge spans 139 feet across the Ottauquechee River on Union Street. The summers in Woodstock are very busy with tourists, for the best photo opportunities, visit on a clear, sunny morning in Spring or Autumn.

Lincoln Bridge - Woodstock, VT
Lincoln Covered Bridge

The Lincoln Bridge is located in the village of West Woodstock, visible from Route 4 and carries Fletcher Hill Road over the Ottauquechee River. Head across the bridge from Route 4 for the best opportunity for parking, as there is no designated parking area – use discretion. The bridge was built in 1877 and spans 136 feet across the river. It is a one of a kind Modified Pratt Truss with an arch. Certainly one you should see while you’re visiting the area.

Taftsville Covered Bridge - Woodstock, VT
Taftsville Covered Bridge

The third covered bridge in Woodstock is the Taftsville Bridge. Located in the village of Taftsville on River Road, this covered bridge is one of the oldest in Vermont. It was constructed in 1836. The Taftsville Covered Bridge is a two span bridge, crossing the Ottauquechee River. It totals 189 feet long with one span being 100 feet and the other 89. For parking, seek a spot along the side of River Road as there is less traffic on that side of the bridge. Be aware, like most covered bridges, there is no designated parking.


Finding a trail to hike isn’t too hard, there’s a few in town, and of course a whole lot of trails scattered all over the Upper Valley of New Hampshire and Vermont. Faulkner Trust and Billings Park Commission lands provides for more than 30 miles of trails throughout the village. (Trail Map)

Mount Peg is one favorite local hike. It begins with a moderate incline as you ascend into the forest from the trailhead parking at Golf and Maple Streets. The trail quickly levels off as you reach the more grassy surface towards the summit. you’ll enjoy wonderful views of Killington Mountain, the Pomfret Hills, Mount Tom and Billings Farm.

Mount Tom - Woodstock, Vermont
Views of Woodstock area from Mount Tom

Mount Tom is another popular hike in Woodstock, VT. The summit can be reached from three popular trails, the Faulkner Trail, the Prosper Trail and the River Street Cemetery Trail. Regardless of which trail you choose to hike, when you reach the summit you’ll be able to enjoy picturesque views of the rolling landscape and the town of Woodstock.

Lastly, Woodstock has been known as a pit-stop for hikers of the Appalachian Trail. The trail crosses over Route 12 as hikers travel towards Killington after crossing the New Hampshire and Vermont boarder. Woodstock makes a great pit-stop because of it’s vast array of shops, restaurants and comforts of home.

Other Points of Interest

There is so much to do in Woodstock, Vermont we’d be hard pressed to list everything here. However, here’s a few things worth checking out and places worth visiting. If you’re moving to the area or even just passing through, these few things should be on your list of things to do in Woodstock, Vermont.

Billings Farm & Museum

Billings Farm can take you on a walk through history of farming in Vermont. It’s a working dairy farm where you can get hands on with things like buttermaking. There are educational opportunities for children and adults of all ages, including school-age and home schooled children.

Billings Farm Cows in Woodstock, VT

The Billings Farm Museum gives visitors a chance to see the history of farm life, including the traditional culture, environment and science. Enjoy the grounds, the animals and historic buildings at Billings Farm. Even enjoy a wagon ride, or a sleigh ride during the snowy months.

Sugarbush Farm

Think cheese. Think Maple Syrup. Think Sugarbush Farm! This is a family farm that is known for is pure Vermont Maple Syrup and waxed cheeses. The products are made right at the farm and you’re invited to learn about the process and take tours of the sugar house, too! The farm is open to visitors year round and you’re invited to stroll the trails to see the sugar maple trees, farm animals and views of the Vermont countryside.

The Sugarbush Farm family is famous for its excellent waxed cheeses and Pure Vermont Maple Syrup made here on our hillside farm.

Union Arena

The Union Arena Community Center in Woodstock, Vermont is a cultural and athletic event center for the community. The arena holds cultural events such as craft fairs, concerts, theater events community gatherings and other community events.

The athletic activities are quiet popular. The Union Arena holds events and sports such as indoor soccer baseball, lacrosse and field hockey in the spring and fall. Ice skating opportunities are offered at Union Arena with six months of winter ice and six weeks of summer ice. This is open for adult and youth hockey as well as figure skating and public skate time. There are exercise programs offered for seniors and handicapped residents as well.

Homes in Downtown Woodstock

Calling Woodstock, VT Home

Woodstock is known as a tourist destination and is has a higher percentage of homes that are owned by out of state residents, vacation homes, than most towns in the Upper Valley. It’s an interesting economic environment that is not often seen in a landlocked town without a major attraction. Although Killington is close by, most of the tourism activity tends to happen during the summer months.

Woodstock’s economy is primarily driven by tourism and the cost of real estate in the village of Woodstock is much higher than the average throughout the villages of Woodstock. The median home value is in the mid-$300,000’s, which is among the highest median values in the Upper Valley.

There are many locally owned and operated businesses in Woodstock. It’s a wonderful place to shop locally and support your local community. Although the businesses in Woodstock employ thousands of people, there are many residents who travel to the larger employment meccas of the Upper Valley, Lebanon and Hanover, New Hampshire.

Although there is an influx of real estate owned as second homes by folks from out of state, there is a healthy population of home owners who live in the town year round. This diversity of residents, coupled with the beautiful town setting, the Green, the historic building and abundance of restaurants, shops and things to do, make Woodstock, Vermont a wonderful place to live and call home.

Woodstock Town Website »