Need a postcard-perfect New England escape with charm and nature? Head to Woodstock! Known for its covered bridges, farm-fresh flavors, and classic village green, Woodstock is one of Vermont’s most picturesque towns. Whether you’re hiking, skiing, or just relaxing with maple syrup and mountain views, Woodstock offers year-round beauty and small-town soul.

Woodstock, VT Highlights:

  • For Adventurous Travelers: Hike to the summit of Mount Tom – Climb through forested trails in Marsh-Billings-Rockefeller National Historical Park for sweeping valley views.
  • For History Buffs: Tour Billings Farm & Museum – Experience a working dairy farm and heritage exhibits exploring Vermont’s rural past.
  • For Shoppers: Browse boutiques around the Village Green – Discover artisan crafts, fine art, books, and Vermont-made goods in locally owned shops.
  • For Couples: Drive the scenic route through Quechee Gorge – Stop for photos, waterfalls, and cozy cafés along Vermont’s “Little Grand Canyon.”
  • For Families: Visit Sugarbush Farm – Sample cheeses and maple syrup, see the sugaring house, and walk farm trails with mountain views.

Best Time to Visit Woodstock, VT

The best time to visit Woodstock is from mid-September to October for fall foliage or December for holiday charm. Summer (June–August) is great for outdoor activities, and winter brings snowshoeing, cozy inns, and nearby skiing.

How to Get to Woodstock, VT

  • If you are traveling by car: Woodstock is located along US-4, about 30 minutes from White River Junction and 2.5 hours from Boston.
  • By Train: Amtrak’s Vermonter line stops in White River Junction, with taxis or shuttles available for the 20-minute ride to Woodstock.
  • By Air: Lebanon Municipal Airport (LEB) is 25 minutes away with regional flights; major airports include Burlington (BTV) and Boston Logan (BOS).

Where to Stay in Woodstock, VT

  • Recommended for Families: 506 On the River Inn – Stylish, family-friendly lodging with a pool, playroom, and riverside views.
  • For Couples: Woodstock Inn & Resort – Historic luxury inn with elegant rooms, spa, golf, and farm-to-table dining.
  • For Budget Travelers: Sleep Woodstock Motel – Retro-inspired, affordable option just outside town with great access to outdoor recreation.

Best Things to Do in Woodstock, VT

Step Into Vermont’s Farming Heritage at Billings Farm

Step Into Vermont’s Farming Heritage at Billings Farm

© Billings Farm

The 270-acre Billings Farm was founded in 1871 by Frederick Billings as an example to farmers in the area of ideas of sustainability, prudent land use and efficiency. Billings brought George Aitken onto the operation in 1884 and as the farm grew to over 1000 acres, they imported sheep, hogs and cows from New Jersey.

Within nine years Billings Farm marked it’s place in history when it won “Champion Heifer of the World” at the World’s Columbian Exposition in Chicago. Today Billings Farm is open to visitors. Families can visit a museum, barns with dairy cows, horses and sheep. Also on site is the original furnished farmhouse from 1890. The farm hosts annual activities and programs.

69 Old River Rd. Woodstock, VT. 05091, Phone: 802-457-2355, Map

Taste Local Cheeses and Maple Syrup at Sugarbush Farm

Taste Local Cheeses and Maple Syrup at Sugarbush Farm

© Sugarbush Farm

The Luce Family has been operating Sugarbush Farm for four generations in central Vermont. Today Betsy Luce and her family carry on the tradition of making and selling award winning cheeses, jams and four grades of Pure Vermont maple syrup.

The Farm operates year round and autumn is the busiest season. Visitors to the farm can observe the various processes of cheese making as well as how the maple syrup is produced. Visitors may try different samples, browse the gift shop, explore the nature trails and pet some of the farm animals, including goats, baby cows, horses, rabbits and chickens.

Sugarbush Farm , 591 Sugarbush Farm Road Woodstock, VT 05091, Phone: 802-457-1757

Hike Through History and Conservation at Marsh-Billings-Rockefeller Park

Hike Through History and Conservation at Marsh-Billings-Rockefeller Park

© Marsh-Billings-Rockefeller National Historical Park

Marsh-Billings-Rockefeller National Historical Park lies Northwest of the village of Woodstock. Charles Marsh built his federal style home here in 1805. Railroad magnate, Frederick H Billings purchased the estate in 1869 and over the years updated the original house in the Queen Anne Victorian style.

In 1992, Billing’s granddaughter, Mary French Rockefeller and her husband Lawrence Rockefeller donated the home to the people of the United States. Today it is on the National Register of Historic Places and is a National Historic Landmark as well. Visitors have access to over 600 acres of varied ecosystems within the park via various roads and hiking trails. There is also a visitor’s center as well as the original mansion and gardens. Tours are available for small and large groups, reservations are recommended.

Marsh-Billings-Rockefeller National Historical Park, 54 Elm Street Woodstock , VT 05091, Phone: 802-457-3368 x222, Map

Climb Mount Tom for Sweeping Valley Views

Climb Mount Tom for Sweeping Valley Views

© Roman Sigaev/stock.adobe.com

Mount Tom is located in the Northwest part of Woodstock. It’s peak measures at 1,357 feet from sea level. In addition to numerous trails to hike and explore, the town holds a variety of events throughout the year on Mount Tom. Among the different trail systems on Mount Tom, the most popular is the Faulkner Trail, constructed 75 years ago by Marianne Faulkner.

Mount Tom is home to a large variety of plant and animal species including some rare species of reptiles. Frederick H Billings, the previous owner prior to the land becoming a park, planted numerous species of trees from around the world. Mount Tom is part of the Marsh-Billings-Rockefeller National Historical Park.

54 Elm Street Woodstock , VT 05091, Phone: 802-457-3368 x222

What to do if you are traveling with kids:

Capture Classic New England Charm at Taftsville Covered Bridge

Capture Classic New England Charm at Taftsville Covered Bridge

© Christian Delbert/stock.adobe.com

Spanning the Ottauquechee River, the Tafstville Covered Bridge is one of the oldest standing covered bridges in the United States. Its unique architecture is of an early craftsman style, possibly linked to early designs from Switzerland.

The bridge was built in 1836 by a native to the area named Solomon Emmons III. His timber design held up for over a century until in was damaged by Hurricane Irene in 2011. After repairs took place, the bridge was once again opened in 2013. The Bridge was added to the National Register of Historic Places in 1973 and is located between Upper River Road and Woodstock Road in Woodstock VT.

Taftsville Covered Bridge , Woodstock, VT 05091

Activities and Attractions for Couples and Singles:

Paddle or Picnic Along the Ottauquechee River

Paddle or Picnic Along the Ottauquechee River

© Vinoverde/stock.adobe.com

The Ottauquechee River flows East from the town of Killington in the Green Mountain until it reaches the Connecticut River in the town of Hartland, 41 miles downstream. Along the way it plunges 165 feet through the Quechee Gorge just outside of the Quechee State Park. A bridge on U.S. Route 4 crosses the gorge and is an ideal location to get a glimpse of the geological marvel.

The U.S. Corp of Army Engineers built a hydroelectric dam at the mouth of the Ottauqechee River and the result is North Hartland Lake. Fisherman frequent the river and lake for its Bass, Northern Pike and in the springtime, Trout.

Ottauquechee River, Woodstock, VT 05091

If You Love Quiet Charm, Visit the Norman Williams Public Library

If You Love Quiet Charm, Visit the Norman Williams Public Library

© Norman Williams Public Library

Situated on the Village Green of Woodstock is the Norman Williams Public Library. The pink sandstone building was built between 1883 and 1884 and is a testament to the history of Woodstock as an unusually literate village during the early 19th century. At the time the library was built, the town had five local newspapers, a medical college, several private academies, and reading circles were very popular.

The library has since undergone a $5 million renovation that highlights the original architecture, while allowing for modern amenities. In addition to providing more than 50,000 reference materials, the library provides computers, printers, copiers and WiFi.

Norman Williams Public Library, 10 The Green, Woodstock, VT 05091, Phone: 802-457-2295

Where to Eat:

Dine Farm-to-Table Style at Scenic Cloudland Farm

Dine Farm-to-Table Style at Scenic Cloudland Farm

© Cloudland Farm

Cloudland Farm was established in 1808 by the Emmons family. They provided sheep, pigs and Jersey cows as well as eggs and apples to the town of Woodstock and surrounding residents. Today, the farm is still in the family operated by Bill and Kathy Emmons. The farm raises chickens, pigs, turkey, and Black Angus cattle in their pastures.

Located on the premises is the Cloudland market where visitors can purchase pottery, pickles, various Vermont cheeses, teas, maple syrups, sodas and teas. Also available for purchase are Cloudland’s Angus beef steaks, sausages, and free range pork, all of which are raised on Cloudland Farm. Cloudland farm offers an authentic farm-to-table dinner made from a combination of ingredients from Cloudland and neighboring local farms.

Cloudland Farm, 1101 Cloudland Rd. Woodstock, VT 05091, Phone: 802-457-2599

Savor a Gourmet Culinary Experience at The Lincoln Inn and Restaurant

Savor a Gourmet Culinary Experience at The Lincoln Inn and Restaurant

© The Lincoln Inn and Restaurant

The Lincoln Inn and Restaurant is not only a Bed & Breakfast, but prides itself in being a culinary destination. The menu changes daily depending on which ingredients are freshest and available. The restaurant offers a seven and twelve course menu as well as a four-course prix fixe option, each paired with hand-selected wines. The 6-acre property is managed by Michelin-trained chef Jevgenija Saromova.

Guests who wish to spend the night can choose from six rooms on the second story of the restaurant. Each of the rooms have views of the Vermont countryside. Lucky guests might get a glimpse of Lord Lincoln and Frankie the Duke of Woodstock, the Lincoln Inn’s beloved resident Whippets.

The Lincoln Inn and Restaurant, 2709 West Woodstock Road, Woodstock, VT 05091, Phone: 802-457-7052

If you are interested in local events:

  • For Holiday Cheer: Wassail Weekend (December) – Horse-drawn carriages, carolers, and holiday markets turn the village into a storybook Christmas scene.
  • For Art Lovers: Woodstock Art Festival (September) – Juried fine art festival with New England artists and live music on the Village Green.
  • For Family Fun: Maple Madness (March) – Celebrate sugaring season with maple-themed treats, sugarhouse visits, and tastings.

Day Trip Itineraries Within 30 Minutes of Woodstock, VT:

  • For Nature Lovers: Quechee Gorge (15 min) – Hike along the rim, enjoy the view from the bridge, and visit the gorge visitor center.
  • For Scenic Drives: Route 100 (25–30 min) – Follow one of Vermont’s most picturesque roads with covered bridges, country stores, and mountain views.
  • For History Buffs: Windsor, VT (20 min) – Visit the Constitution House, artisan shops, and Harpoon Brewery along the Connecticut River.
  • For Family Fun: Vermont Institute of Natural Science (VINS) (15 min) – Live raptor shows, forest canopy walk, and interactive nature exhibits in Quechee.
  • For Wine Lovers: Fable Farm Fermentory (25 min) – Sample ciders and natural wines made from Vermont-grown fruits in a bucolic hilltop setting.

Frequently Asked Questions:

  • Where is Woodstock located?
    • The small, picturesque New England town of Woodstock is situated on the easternmost border of Vermont with New Hampshire.
  • Who was the first settler of Woodstock?
    • James Sanderson was the first settler in 1768, and by the time of the Revolutionary War, the population had reached 1,600 people.
  • What is the population of Woodstock today?
    • Today, Woodstock has just over 3,000 inhabitants and retains its small-town charm.
  • What is the most popular tourist attraction in Woodstock?
    • The most popular tourist attraction in the area is the Billings Farm and Museum, a historic site showcasing Vermont's agricultural heritage.
  • Are there inns and restaurants in Woodstock?
    • Visitors will find a number of charming inns and restaurants in Woodstock.
  • What historic architecture can be seen in Woodstock?
    • The Village Green is the central square, and a stroll around it reveals a number of Federal Style, Georgian, and Greek Revival homes.

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