Top 12 Best Things to Do in Woodstock Vermont

You’ll find plenty of things to do in Woodstock VT, a vibrant community with a charming downtown and historic inn, surrounded by beautiful landscapes, and outdoor recreation.

A farm in Woodstock Vermont

Named “the prettiest small town in America” by Ladies Home Journal in 2011, Woodstock, Vermont is what most people imagine the quintessential New England village to be.

This town has it all – a charming downtown with red brick buildings, a village green, a stunning inn as well as skiing, hiking, and golf nearby, and even a historical mansion. It’s no wonder Woodstock is one of the more popular towns to visit in Vermont.

Located slightly below the state’s middle, Woodstock is only a 30-minute drive west from Hanover, New Hampshire, home of Dartmouth College, and a 30-minute drive east from Killington, Vermont, home to one of the largest ski mountains in the east.

You’ll find plenty of things to do in Woodstock VT, in all seasons, but the height of the tourist season is typically the fall foliage season around late September and early October.

Summer months are also popular when the weather is warm and outdoor activities like hiking, biking, and golf are available. The winter months attract tourists who come to enjoy both downhill and Nordic skiing as well as snowshoeing.

Top Things to Do in Woodstock VT

These are the absolute best things to do when visiting Woodstock.

Stroll through downtown Woodstock village

Downtown Woodstock - among the things to do in Woodstock VT

One of the main attractions of Woodstock is its quaint New England downtown full of historic architecture, unique shops, art galleries, a village green, and restaurants.

One popular spot is F. H. Gillingham & Sons, a general store that’s been in operation since 1886 and offers everything from groceries and clothing to hardware and housewares.

Book lovers will also want to stop into The Yankee Bookshop, the oldest continuously operated independent bookshop in Vermont.

Art aficionados will want to explore the several galleries in the town including the Woodstock Gallery, which features both local and national fine art, and the Collective, a collection of arts and crafts from local artists.

If you get hungry or want a bite to eat while strolling, be sure to stop in at the Mont Vert Cafe – a delightful place to have a cup of coffee, a pastry, or a sandwich for lunch. A good, casual dinner option is Worthy Kitchen, a short drive from downtown, which features farm-to-kitchen comfort food such as burgers, salads, and even poke bowls.

Explore the Marsh-Billings-Rockefeller Mansion

The Marsh Billings Rockefeller Manison in Woodstock Vermont
Photo credit: United States Library of Congress’s Prints and Photographs division / Creative Commons

Not far from downtown Woodstock is the Marsh-Billings-Rockefeller Mansion and National Park, a 643-acre property that consists of a mansion as well as gardens, hiking trails, and picnic areas.

The brick mansion was built in 1805 by Charles Marsh and designed in the Federalist style but was purchased 64 years later by the prominent lawyer Fredrick Billings who significantly enlarged the house and remodeled it in the Queen Anne Style.

In 1954 the property was inherited by Billing’s granddaughter, Mary French Rockefeller who adapted the home for modern living. The home remains the way the Rockefellers left it in 1997.

The original owner’s son, George Perkins Marsh, was a diplomat and conservationist who wrote Man and Nature in 1864, a groundbreaking book about environmentalism at the time. He’s considered one of the fathers of the American conservation movement and visitors to the mansion and national park will learn about the history of conservation.

Guided tours of the mansion are available between late May and October 31st. It’s advised to make reservations in advance as there is limited space on the tours. These reservations can be made up to 60 days in advance. (54 Elm Street)

Visit the Billings Farm and Museum

The Billings Farm and Museum - among the things to do in Woodstock VT
Photo credit: David Fulmer / Flickr

Just across the street from the mansion, is the Billings Farm and Museum. This working farm is a tribute to Vermont’s rural heritage and showcases traditional farming practices and livestock. It’s an especially fun place for animal-loving kids to visit.

While exploring the farm, visitors can see several farm animals such as cows, sheep, horses, and chickens. There’s also a museum that features exhibits of the history of the Billings family, their farm, and the dairy industry.

Daily programs include milking, cheese-making, and butter-churning demonstrations as well as wagon rides. There’s also a gift shop and dairy bar (occasionally open) on the property. Hours vary by season so check the website before you visit. Admission is $17 for adults, and $10 for children while children under 3 are free. Other admissions discounts apply. (69 Old River Road)

See related: 10 New England Small Towns That Feel Like Stars Hollow

Visit or Stay in the Historic Woodstock Inn and Resort

The Woodstock Inn in Vermont

Right in the heart of the downtown, across from the village green, is the Woodstock Inn and Resort.

Built in 1892, by the Rockefeller family, this inn has been renovated and expanded over the years but has kept its original New England charm. It’s been the host of many famous guests over the years including President Calvin Coolidge and his family, and actors Robert Redford and Paul Newman.

The inn offers a variety of accommodations, including guest rooms, suites, and private cottages. You’ll also find a full-service spa, a pool, and two restaurants, The Red Rooster, and Richardson’s Tavern, and access to a golf course. (14 The Green)

Visit the Sugarbush Farm

A goat in a field

Among the fun things to do in Woodstock VT is to visit Sugarbush Farm.

This family-owned farm offers visitors the opportunity to learn about maple syrup production and sample various grades of syrup. It also has a cheese-making facility where cheese is made from scratch using milk from the farm’s own cows.

In addition to maple syrup and cheese, the farm also sells various locally-made products such as honey, jams, and mustard. Visitors can take a self-guided tour of the farm, hike the farm’s scenic trails, and enjoy a picnic with beautiful views of the surrounding countryside. Hours are 9 AM – 5 PM every day. Admission is free.

Go hiking or biking

A hiking trail in Vermont

Vermont is a haven for outdoor enthusiasts and Woodstock’s no different. There are plenty of opportunities for hiking and biking in the area as the town is surrounded by the Green Mountains. Furthermore, the grand 2,200-mile Appalachian Trail passes through Woodstock, offering breathtaking views of the surrounding landscape. Hikers can pick up the trail by driving north on Route 12 and parking in a lot just across from 3096 Barnard Road.

Mount Tom is another popular hiking trail that can be picked up at the Billings Farm and Museum near the visitor’s center. Along the trail, you’ll walk through the Marsh-Billings-Rockefeller property, and at the summit, on a clear day, you’ll see all of downtown Woodstock below.

For bikers, the Woodstock Area Mountain Bike Association Trails maintains several trails on Mount Peg, near the Woodstock Aqueduct, and at the ski resort, Saskadena Six (formerly called Suicide Six) located in Pomfret. There are over fifty trails in all that range from beginner to advanced.

Visit a local ski resort for Nordic or downhill skiing

A ski mountain in Killington Vermont
Killington Mountain

Among the fun outdoor things to do in Woodstock VT is to go skiing. You’ll find both Nordic and downhill skiing options either in or not far from Woodstock.

The Woodstock Inn operates the Woodstock Nordic Center which provides 45 km of groomed trails throughout nearby Mount Tom and Mount Peg. Fatbikes and snowshoes are also permitted to use the groomed trails. Ski and snowshoe rentals as well as trail passes can be purchased at the center which is at the Woodstock Country Club (76 South Street).

Downhill skiers have three nearby options near Woodstock. First, the small Ski Quechee is a great option for families and beginner skiers, provides 13 trails, and is a 10-minute drive from the center of Woodstock (3268 Quechee Main Street, Quechee). Saskadena Six (formerly called Suicide Six) has 24 trails and is about a six-minute drive north from the center of Woodstock (247 Stage Road, South Pomfret). And finally, one of the most expansive mountains in all of New England with 155 ski trails and 22 chair lifts, can be found in Killington, a 20-minute drive west down Route 4 (3861 Killington Road, Killington).

Check out the Woodstock Farmers Market

Food lovers will want to check out the Woodstock Farmer’s Market, a year-round facility that offers locally-grown produce, cheeses, meats, and baked goods. You’ll also find a deli and prepared foods section in the market. In addition to the delicious food offerings, visitors can also enjoy live music and other entertainment, making it a fun and lively community gathering spot. (979 West Woodstock Road)

Go on a hot air balloon ride

A small hot air balloon above fall colored trees

Among the fun things to do in Woodstock VT is to see the town and surrounding area in a hot air balloon. This is an especially good way to take in the Green Mountain’s changing colors in the autumn. The local company, Quechee Balloon Rides, meets customers on the Quechee Village Green and prices are approximately $350 per person.

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Drive by local covered bridges

Middle Bridge - seeing covered bridges is among the things to do in Woodstock VT
Woodstock’s Middle Bridge

Woodstock is the perfect area to take in a number of old New England covered bridges. Middle Bridge is only a few steps from the town green on Mountain Avenue. This quaint bridge has both an area for cars and pedestrians. And the Elm Street Bridge is less than a mile away on – you guessed it – Elm Street.

While driving to the village of Quechee along Route 4, you’ll also have the chance to see the Taftsville Bridge – a beautiful red bridge that straddles the Ottaquechee River. Other covered bridges on or near Route 4 include the Middle Covered Bridge, the Quechee Gorge Bridge, and in the other direction going west out of town, the Lincoln Covered Bridge.

See related: 4 Charming Covered Bridges in Woodstock Vermont

Attend a concert or event at the Woodstock Town Hall Theatre

Among the fun things to do in Woodstock VT is to attend a concert or event at the Woodstock Town Hall Theatre. Just steps away from the village green, you can’t miss this red brick building that was once the town hall.

Today, this historic venue hosts a variety of music concerts, film screenings, theater performances, and cultural events throughout the year. The quaintness and charm of the building create an intimate atmosphere making it a unique and memorable setting for any performance. (31 The Green)

Explore Quechee Vermont and its famous gorge

A view of the Simon Pearce Factory and Store in Quechee VT
A view of the Simon Pearce factory and store

Just a 12-minute drive east of Woodstock is the tiny but charming village of Quechee. The village is best known for its incredible gorge, familiarly called the “Grand Canyon of the East” given its deep, narrow groves carved out by the Ottauquechee River.

Also in Quechee, you’ll find the headquarters of Simon Pearce, a renowned glassblowing and pottery store. On the lower level of the shop, you’ll be able to step into the glassblowing factory and watch skilled artisans create beautiful glassware by hand. While down below, take a minute to step outside on the balcony to take in the waterfall and nearby covered bridge. Upstairs, you’ll be able to purchase some of the company’s glassware and hand-thrown pottery as well as have a meal at the award-winning restaurant.

(As a GetYourGuide affiliate, I earn from qualifying purchases at no extra cost to you.)

A photo of Kerry Flatley leaning against a wall

About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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