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Woodstock, Vermont Travel Guide


Woodstock Inn and Resort | Woodstock Vermont Travel Guide
Woodstock Inn and Resort

Woodstock, Vermont is one of New England’s most picturesque and inviting towns. The village is home to a charming main street, tree-lined green, covered bridge, and the stately Woodstock Inn and Resort. Our Woodstock, Vermont travel guide will provide you with an overview of this quaint Vermont vacation destination.

Calf | Billings Farm and Museum | Things to do in Woodstock Vermont | New England
Calf | Billings Farm and Museum

It’s difficult to drive through Woodstock without stopping to stroll. Downtown is filled with one-of-a-kind shops and a central green that is surrounded by elegant Georgian colonials and Greek Revival buildings. Wide sidewalks and a covered “kissing” bridge entice visitors to stop and explore. On the edge of town, the Billings Farm beckons visitors to learn about the Green Mountain State’s rural culture.


Use our guide to discover all the best things to do in Woodstock, Vermont, and the surrounding area.

Central Street | Woodstock, Vermont | New England Travel Destination
Central Street | Woodstock, Vermont
Woodstock Vermont Travel Guide At A Glance | New England Travel Destinations
Statue Marsh-Billings-Rockefeller National Historic Park | Woodstock Vermont

For more information on New England travel destinations read our articles on:

Farm | Windsor County | Woodstock Vermont Travel Guide | New England
Farm | Windsor County

AREA OVERVIEW

Woodstock, and the neighboring towns of Quechee and Windsor, are located in Windsor County, Vermont. The district sits at the base of the Green Mountain National Forest between Rutland, Vermont and Hanover, New Hampshire. The landscape is made up of gently rolling hills dotted with farms, taverns, and New England-style dwellings. Along scenic Route 4, there are a number of reinvented factory buildings filled with textile and antique galleries and shops.

Antiques Collaborative | Quechee Vermont | Woodstock Vermont Travel Guide
Antiques Collaborative | Quechee

The three towns sit in a pocket between Interstates 89 and 91, and the Crossroad of Vermont Byway (Route 4). Windsor County roads are punctuated by pastureland, no-stoplight villages, and stunning rural landscapes. To fully enjoy the area, a personal vehicle is recommended.


Our Woodstock, Vermont travel guide will provide an overview of the area and things to do in Woodstock, Windsor, and Quechee, Vermont.

Quechee Covered Bridge | Woodstock Vermont Trave Guide | New England Travel Destinations
Quechee Covered Bridge

Woodstock, Vermont

Woodstock’s center revolves around Central and Elm Streets, and the village green. Central and Elm are lined with locally-owned shops, boutiques, and restaurants. Some of these businesses, like F. H. Gillingham & Sons General Store, have been in town for generations. The graceful town-green steals the show, though. It is flanked on one side by the landmark Woodstock Inn and Resort; and on the other, by Middle Covered Bridge.

Shopping Woodstock, Vermont | New England Travel Destinations
Shopping Woodstock, Vermont

Quechee, Vermont

Just a short 7 miles away from Woodstock, on the Ottauquechee River, the village of Quechee draws visitors with its astounding 165’ deep Quechee Gorge (aka “Vermont’s Grand Canyon”). The road leading to and from Quechee Gorge is a menagerie of upscale antique malls, breweries, and shops selling cheese and maple syrup. A short distance from the gorge, in tiny Quechee village, there is a covered bridge, waterfall, and Simon Pearce factory store to explore.

Quechee Gorge | Best Things To Do in Woodstock Vermont | New England Travel Destinations
Quechee Gorge

Windsor, Vermont

The town of Windsor is located on a curvy roadway about 11-miles south of Woodstock. Established in 1777, Windsor is known as the “Birthplace of Vermont.” Its downtown is not as fashionable as Woodstock’s. Nevertheless, Windsor has a lot to offer. Visitors can explore the lovely Cornish-Windsor Bridge, hike Mt. Ascutney, and shop Windsor’s Artisans Park with a brewer, distillery, glass factory, and river outfitter (to name a few) onsite.

Fire Tower | Mount Ascutney | Woodstock Vermont Travel Guide
Fire Tower | Mount Ascutney

WHEN TO VISIT

Woodstock, Windsor, and Quechee are 4-season New England travel destinations. The area is as beautiful (and busy) in the snowy winter as in bloom of summer or brilliant foliage of autumn. Visitors should be aware that the spring season in New England tends to be the quietest season due to the mud, mosquitoes, and brown landscapes before the plants and trees buds.

Autumn on the Town Green | Woodstock Vermont Travel Guide | New England
Autumn | Woodstock Green

During the holidays, the town of Woodstock is full of twinkling lights, decorated store windows, and festive door stoops. Summer brings hikers, bikers, and vacationers. Weekends in the fall are busy with leaf-peepers and bus tours.

Antique Shop | Best Things To Do in Woodstock Vermont
Antique Shop

WOODSTOCK, VERMONT HOTELS

There are many types of accommodations in the Woodstock, Vermont area. There are historic inns, independent motels, and resorts for all budgets. Look for lodgings near Woodstock center if you want to walk to shopping and restaurants. For a quieter environment, search in Quechee or Windsor.

Marsh-Billings-Rockefeller National Historic Park | Woodstock Vermont | New England Travel Destinations
Marsh-Billings-Rockefeller National Historic Park

Woodstock Inn and Resort: The upscale, luxury resort sits across from the Woodstock village green. The distinctive accommodations include light filled rooms, many with wood-burning fireplaces. There is a pool, tavern, and dining room on property. The resort specializes in golf, ski, spa, and activities packages. Rooms start at around $599 per night.

Windsor Vermont | New England Travel Destinations
Windsor, Vermont

The Shire Woodstock: Perched on the shore of the Ottauquechee River, the independently-owned Shire Woodstock is within walking distance of downtown Woodstock. The hotel’s 43 rooms feature a refrigerator in every room. The grounds offer a garden and picnic area to enjoy. Rooms start at around $176 per night.

Windsor Artisans Park | Woodstock Vermont Travel Guide | New England
Windsor Artisans Park

The Vesper Bed & Breakfast: The inn is an 1835 Greek Revival home situated nearby the village green in Woodstock village. The family-run property features free wifi and candlit breakfast. Common areas feature a wood burning stove and porch. Rooms start at around $212 per night.

Church | Windsor-Brownsville | Woodstock Vermont Travel Guide
Church | Windsor-Brownsville

WOODSTOCK, VERMONT RESTAURANTS

Woodstock, Quechee, and Windsor have many types of eateries at different price ranges. Many establishments advertise locally-sourced ingredients and vegetarian menu items. Regional favorites include foods flavored with Vermont-made maple syrup, cheddar cheese, apples, cider, homemade donuts, pies, and wood-fired breads. Visitors will find a wide selection of restaurants, pubs, breweries, bistros, and cafes to choose from.

Billings Farm and Museum | Woodstock Vermont Travel Guide | New England
Billings Farm and Museum

THINGS TO DO IN WOODSTOCK, VERMONT

1. Spend an afternoon strolling the shops and galleries of Woodstock’s downtown.

2. Learn how to milk cows at the Billings Farm Museum (Woodstock’s outdoor history museum).

3. Go on a scenic ride of the area’s four covered bridges (Middle, Quechee, Taftsville, and Cornish-Windsor).

4. Take a Segway Tour through Quechee Gorge State Park.

5. Hike to the summit of Windsor’s Mt. Ascutney, and climb the fire tower.

6. Go antiquing along Route 4 at the Quechee Antiques Collaborative and Quechee Gorge Village.

7. Take a guided tour of the mansion and gardens of the Marsh-Billings-Rockefeller National Historic Park. Hike its expansive grounds.

8. Visit the businesses of the Artisans Park Windsor Vermont. The park is home to Harpoon Brewery, Great River Outfitters, SILO Distillery, Blakehill Preserves, Simon Pearce, Vermont Farmstead Cheese, and others.

Mountain Biking | Windsor County | Woodstock Vermont Travel Guide
Mountain Biking | Windsor County

9. Drive through the Green Mountain National Forest to Killington Ski Resort for a gondola ride.

10. Schedule a spa day at the luxurious Woodstock Inn and Resort.

11. Hike the Ottauquechee River Trail. The 3-mile walking path begins at Woodstock’s East End Park and runs along the river past woods, fields, and bogs.

12. Rent e-bikes at Woodstock Wheels and cruise the glorious landscapes and backroads of Vermont.

Scenic Drive Windsor County | Things to do in Woodstock Vermont
Scenic Drive Windsor County

Don’t forget to bring home some maple syrup. Safe travels, Laura and Randy


For more information on New England travel destinations read our articles on:


Shops of Woodstock, Vermont | New England Travel Destinations
Shops of Woodstock, Vermont

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