Blake Walsh

20 Best Things to Do in Woodstock, VT

  • Published 2022/08/31

Woodstock, Vermont, a picture-perfect New England hamlet, has been named the nation’s prettiest by visitors.

It is a small town in the eastern part of the state, about 15 miles from the New Hampshire state line.

It’s a terrific spot to see and do everything that makes Vermont unique, including beautiful buildings, breathtaking natural beauty, a world-renowned farm, fantastic restaurants, unique shops, and warm Vermont hospitality.

It is a charming destination year-round, with much to do regardless of the season.

On the other hand, most visitors flock to the town during fall because of the brilliantly colored foliage.

You may use one of the many online maps of fall foliage to plan your trip around the season’s peak hues.

Just the trip to Woodstock, Vermont, is half as much enjoyable as exploring this scenic town.

BTV, Burlington’s international airport, is the nearest major airport at a distance of 86 miles.

You may then rent a car and go on that long-awaited New England road trip.

Read on to find out what activities you can try in Woodstock, Vermont.

Meet Farm Animals at the Billings Farm & Museum

Beautiful View of Billings Farm & Museum

Reimar /

Frederick Billings established Billings Farm in 1871 as an example of sustainable farming, wise land management, and efficiency for other farmers.

In 1884, the owners hired George Aitken, and as the farm expanded to over 1000 acres, it began to import livestock from New Jersey, including sheep, hogs, and cows.

Nine years later, World’s Columbian Exposition in Chicago awarded the “Champion Heifer of the World” title to Billings Farm.

Daytime view of Billings Farm & Museum

Harvey Barrison from Massapequa, NY, USA, CC BY-SA 2.0, via Wikimedia Commons

Children and their families will enjoy visiting a farm museum and seeing the dairy cows, horses, and sheep that live there.

You will also find here the original 1890 farmhouse.

Every year, the farm organizes a variety of events and initiatives.

Walk Across the Covered Bridge Trio

Exterior of the Taftsville Covered Bridge

Jon Bilous /

Woodstock has three historic covered bridges.

While all three are passable by car, it also has a pedestrian path, making it simple to stop by and wonder about the past building methods.

The bridges were covered not to protect those passing through them but to preserve them.

Maybe that’s why so many still stand?

View from inside the Taftsville Covered Bridge

Yeokum Photography /

The first one is the Taftsville Covered Bridge, a National Historic Landmark.

The long brilliant red bridge is visible from Route 4 into town. It was built in 1836 and spanned 189 feet across the Ottauqueechee River.

Next, the Lincoln Covered Bridge, also in the NRHP, is a 14-foot-wide single-span near the town’s south end.

The Lincoln Bridge, established in 1877, spans the Ottauqueechee River.

Exterior of the Lincoln Covered Bridge

Felix Lipov /

This bridge is unique because it is the only wooden “Pratt Truss” bridge known in the U.S.

Just feet from the town green is one of Vermont’s most photographed covered bridges.

On Union Street, the Middle Bridge has a unique construction narrative.

According to the Vermont Covered Bridge Society, the bridge was built nearby and dragged across the river by Ben and Jo in July 1969.

Exterior of Middle Bridge

Heather Raulerson /

Lodge at Woodstock Inn and Resort

Outside View of Woodstock Inn and Resort

jenlo8 /

The Woodstock Inn and Resort is a five-star hotel situated at the heart of the city.

To give guests a taste of traditional New England hospitality, the inn showcases the best of Vermont artistry at every turn.

For year-round activities, town strolls, or just a peaceful retreat, the inn’s 142 hotel rooms and suites are ideal.

A classic reading room with checkers and chess tables, as well as a pub-style meeting room with pool tables, a shuffleboard table, and a lumber fireplace, are available to guests inside.

Winter guests will appreciate the inviting lobby with its stone fireplace and enough seats for reading or resting.

Large maple trees shade the front and back lawns, making them ideal for relaxing with a summer beverage.

Learn Cheese-Making at Sugarbush Farm

For four generations, the Luces has owned and operated Sugarbush Farm in central Vermont.

With the help of Betsy Luce and her family, the farm still produces and sells Pure Vermont maple syrup today.

The cheeses and jams are award-winning, too.

It runs all year-round, but it’s busiest in the fall.

Here, you may see the different cheese-making operations up close, as well as the maple syrup production process.

Samples are available for visitors to try.

You may also check out its gift store and nature trails and pet its farm animals, such as baby goats, cows, horses, and chickens.

Admire the Breathtaking View on Mount Tom

Tree log with a quote at Mount Tom

AprilDC /

Mount Tom is a mountain in Woodstock, New York, located to the northwest of downtown. It’s 1,357-foot high at its highest point.

The community of Mount Tom hosts various activities throughout the year, including hikes and explorations on the mountain’s many paths.

The Faulkner Path, built by Marianne Faulkner 75 years ago, is the most popular of Mount Tom’s trail systems.

Plant and animal life abound on the mountain, including several endangered species of reptiles.

Before becoming a park, the land’s former owner, Frederick H. Billings, planted a wide variety of tree species from all over the world.

There is a national historical park atop Mount Tom that includes parts of the Marsh-Billings-Rockefeller area.

Swim at the Ottauquechee River

View of Ottauquechee River

jenlo8 /

Ottauquechee river spot in Taftsville is 3.6 miles away from downtown Woodstock.

Adventurers wishing for a more exhilarating splash can discover a rope swing on Old River Road, close to the historic Taftsville Covered Bridge.

The waters of Ottauquechee River


To get to the broad, tranquil water channel, you may either swing from a long, knotted rope or down a steep hill.

Most of these swimming areas are unsupervised, so be cautious and check the conditions before you go.

It is also a dog-friendly swimming hole here, so feel free to bring your four-legged friends along for the trip.

Trees surrounding Ottauquechee River

Clarisse Gamblin /

Learn About Falcons With New England Falconry

The New England Falconry Association works with the Woodstock Inn & Resort to offer falconry education to Woodstock.

New England Falconry operates in Hadley, Massachusetts but occasionally brings its shows to the Woodstock Inn & Resort.

The group teaches about raptor adaptations, conservation, permits, and the history of falconry and offers free-flying Harris hawk demonstrations for attendees.

Woodstock, Vermont’s Historic Rutherford Barn, serves as the site of the falconry center.

Chris Davis, a master falconer, has been sharing his knowledge of raptors and falconry since 1985. The experience you’ll have with him and his helpful team will be one you’ll never forget!

As a souvenir, why not take home some New England Falconry apparel?

Check Out Fossil Glass’ Artisan Glasswares

Are you looking for some decorative or kitchen-use glassware?

Fossil Glass, a quaint shop in Woodstock, is the place to be.

It mainly features the works of the owner, Christina, who is a very skilled glass artist.

The majority of the items are either glasses, bowls, or plates in shape.

While they are too lovely to use, they are also an excellent addition to your craft collection.

Given the outstanding quality, the prices are pretty fair.

There is such a wide range of items and colors to choose from.

Fossil Glass is an exciting place to visit and will almost certainly tempt you to purchase something.

Drop by Woodstock Town Crier

Sign of Woodstock Town Crier

James Kirkikis /

Before the age of social media, the preferred means of finding out what was going on in town was via an actual person who would stand in a public area and yell out news and events.

The Woodstock Town Crier, a public chalkboard in Woodstock, Vermont, continues this tradition.

The old-fashioned message board sits on a small plot of grass in the town’s center.

Town criers were notably popular in Colonial New England, inspiring many local newspapers that still carry the title.

Chalkboard at Woodstock Town Crier

James Kirkikis /

However, Woodstock’s community board reflects the original stance better than any newspaper by simply publishing local news and activities.

People can write public events on the board as if they were whispering into the ear of old public employees.

Surprisingly, the Woodstock Town Crier does not get vandalized, demonstrating the town’s respect for its history and traditions.

The Woodstock Historical Society also maintains this historic site.

Travel Back in Time at Historical Society of Woodstock Headquarters

An association of artists, authors, scholars, and local people came together in 1929 to form the Historical Society of Woodstock (HSW).

Apart from its gallery space, which lies within Woodstock’s historic Eames House located at Comeau Drive, the Historical Society also has an extensive archive including paintings, prints, drawings and sculptures, and textiles and photographs.

The Historical Society also has a collection of letters and documents, books, manuscripts and correspondence, film and sound recordings, and antique tools.

An incredible array of exhibitions, public programs, and research are made possible by the archive.

See the Different Works of Art at Collective

Collective is a gallery in picturesque and historic Woodstock, Vermont, owned and run by its members as a co-op.

Each member has spent years honing and developing their trade to the highest possible level of quality.

Marvelous and uncommon things created to the finest quality fill the gallery, making for lovely purchases to enjoy for years and years to come for the purchaser.

To experience the enchantment of this 19th-century setting, walk inside and look about at our hand-made masterpieces made from materials like glass, fibers, ceramics, metal, and even paper.

The artists at Collective give you a creative mix of finely polished and expertly produced things for everyday use – be it cups, bowls, one-of-a-kind apparel and jewelry, unique lamps, or art for your walls.

Explore Marsh-Billings-Rockefeller National Historic Park

View of  Marsh-Billings-Rockefeller National Historic Park

Reimar /

Across the Billings Farm, you may find the Marsh-Billings-Rockefeller National Historic Park, the only national park unit in Vermont.

The National Park Service describes this particular park as “the only national park to convey the tale of preservation history and the developing character of land management in America,” a combination of nature preserve and history museum.

Perkins Marsh State Park takes its name from George Perkins Marsh, a 19th-century American conservationist who pioneered the preservation movement in the 1830s and 1840s.

Trees at Marsh-Billings-Rockefeller National Historic Park

Reimar /

In 1869, Frederick Billings purchased the estate and turned it into a modern dairy farm.

Even after Mary French Rockefeller and Laurance S. Rockefeller took over the land, they kept the family tradition of responsible farming and forestry.

In 1871, they founded the Billings Farm & Museum, and in 1992, they donated the estate to the U.S. government.

Wooden bench at Marsh-Billings-Rockefeller National Historic Park

Jollieduck, CC BY-SA 4.0, via Wikimedia Commons

Watch Local Performances at Woodstock Town Hall Theatre

Originally built as the town’s opera house in 1900, Pentangle Arts Council presently manages the Woodstock Town Hall Theatre.

Over 250 days a year, the Town Hall Theatre hosts a wide range of movies and live productions such as theater, music, dance, exhibitions, and classes and workshops.

It has a gorgeous neoclassical proscenium architecture with 390 seats and outstanding natural acoustics.

The Pentangle Arts Council’s website has complete information on the film and performance schedule.

Bring Home a Piece of Woodstock From F.H. Gillingham & Sons General Store

Outside View of F.H. Gillingham & Sons General Store

Jsbillin, CC BY-SA 4.0, via Wikimedia Commons

Frank Henry Gillingham founded his store in the heart of this New England town in 1886 when Woodstock, Vermont, was a pretty different place in terms of size and shape.

The community has reverently maintained the physical structures as well as the spiritual essence from the old days.

Townsfolk’s faces have changed, and the store’s merchandise has altered, but the family running it has remained constant.

People going in F.H. Gillingham & Sons General Store

James Kirkikis /

The current owners of this store are both F.H. Gillingham and Franklin Billings’ descendants.

It’s a family tradition that Frank & Jireh Billings are happy to continue, as their great-grandfather did 132 years ago.

Release Your Stresses at The Spa at the Woodstock Inn

The Woodstock Spa offers personalized spa treatments to help you de-stress.

The spa, which is just next door to the Woodstock Inn, provides a welcome break from the everyday.

Guests can rest for up to an hour between treatments in a sun-filled lounge space on the second and third floors.

Meanwhile, the hot tub outdoors is waiting to ease any stress that has built up.

Ten individual treatment rooms are available, steam and sauna rooms, and locker rooms for ladies and men.

In the lounge, there are refreshments and flavored water for your enjoyment.

Nothing except peace and tranquility!

Appreciate the View at Woodstock Country Club

The Woodstock Country Club’s golfing facility is gorgeous in pristine Vermont countryside, surrounded by the green Kedron Valley and with breathtaking views of Mount Peg.

Robert Trent Jones, Sr. built the prestigious 18-hole course.

It was ranked among the top 100 golf resorts by Golf Magazine and had a par 70 course that provides players of all skill levels with an amazing experience.

The Woodstock Country Club’s practice areas include a short game section, training putting green, and a comprehensive driving range, including ten hitting stations.

Additionally, visitors can schedule private and group instruction appointments with the PGA Professional team.

View the Artworks at Gallery on the Green

For over 14 years, modern realism Chip Evans has been the Gallery’s featured artist.

The mission of Chip and his partner Opal is to provide tourists with the greatest, most exquisite fine art that captures the region’s distinct beauty and rich history.

For years, Chip Evans has painted more than 300 oils depicting the breathtaking landscapes of New England.

Settle back and take in the artwork of more than 30 original paintings.

During the summer and fall weekends, go to Gallery on the Green for some great jazz and cuisine.

Visit Norman Williams Public Library

Exterior of the Norman Williams Public Library

Kenneth C. Zirkel, CC BY-SA 4.0, via Wikimedia Commons

The Norman Williams Public Library is situated on Woodstock’s Village Green.

The structure made of pink sandstone was constructed between 1883 and 1884.

It is evidence of Woodstock’s past as an extraordinarily literate community during the earlier 19th century.

Building sign of Norman Williams Public Library

jenlo8 /

The town had five neighborhood newspapers, a medical school, many private schools, and reading groups that were highly well-liked when the library was constructed.

Since then, the library has undergone modifications that preserve the historic building while adding contemporary conveniences.

The library offers WiFi, computers, printers, copy machines, and more than 50,000 reference materials.

Purchase Local Products at Cloudland Farm

The Emmons family has owned Cloudland Farm, a multifaceted working farm, since 1908.

The four-mile beautiful journey up Cloudland Road and the breathtaking sights are all aspects of the Cloudland adventure.

The farm’s land is traversed by the Appalachian Trail, which is accessible to hikers 365 days a year.

The Cloudland Farm Market sells Cloudland’s delectable pure Angus beef cuts, ground beef, barbecues, sausage, beef jerky, and cucumbers if you want to bring a piece of the farm back with you.

The Farm Market also sells local products such as maple syrup, dairy foods, teas, beverages, handcrafted goat’s milk soaps, roller pins, hardwood cheese boards, and Laura White ceramics.

Create an Exclusive Item to Keep at Farmhouse Pottery

Old-fashioned potters at Farmhouse Pottery utilize essential equipment and have a firm commitment to authenticity and the creative process.

The most extensive studio pottery facility in the United States and our full selection of contemporary home furnishings are housed at their flagship store, which is situated in the iconic Vermont town of Woodstock.

They contend that the heart of communities is made up of farmers, artisans, and makers and that the farm-to-table movement is not just a fad in the food world but rather the restoration of a more ecological way of life and set of values.

They are reintroducing people to this way of life and establishing its role in contemporary culture via their craft and day-to-day activities.

Set up a clay date and create your exclusive artisan keepsake while learning about the process of producing pottery from one of their expert potters.

Final Thoughts

Places like Woodstock, Vermont, which has a rich history, are slowly fading with time.

Fortunately, this city manages to maintain its vibrancy and sense of community in the 1800s.

It’s a year-round vacation spot full of history and outdoor activities for the whole family.

Visit this place, and you’ll instantly fall in love with its charm!

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