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Woodstock, Vermont 3 Day Itinerary


Cornish Windsor Covered Bridge | Woodstock Vermont 3 Day Itinerary | Vermont Vacation Destination
Cornish Windsor Covered Bridge

The town of Woodstock is a much-loved Vermont vacation destination. The New England-style village is built around a pretty green and upscale shopping district with many independently owned restaurants, markets, and boutiques. Our Woodstock, Vermont 3-day travel itinerary will help you enjoy all the area’s best things to do.

Woodstock Village | Things to do in Woodstock Vt | New England Travel
Woodstock Village

The colonial houses of Woodstock village are surrounded by Vermont’s Green Mountain National Forest and miles of farm land. Just a short distance from the historic inns of Woodstock, visitors can be hiking, skiing, and taking scenic drives past the areas many rivers and covered bridges. As in most of New England, public transportation is sparse. The area is best traveled by private vehicle.

Windsor County | Woodstock Vermont 3 Day Travel Itinerary | New England Travel Destination
Windsor County

Woodstock is a 4-season New England travel destination. Most businesses are open year-round, but change hours seasonally. Always check ahead before confirming your plans.

Woodstock Vermont 3 Day Travel Itinerary | New England
Billings Farm Museum | Woodstock Vermont Things To Do | New England Destinations
Billings Farm Museum

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Day 1: Explore Woodstock Village, the Green, and Middle Covered Bridge

Take the day to explore the charming village of Woodstock. Walk the downtown area and explore the businesses of Central and Elm Streets. The area is full of many one-of-a-kind shops and galleries. The F. H. Gillingham General Store has been in town over a century. The Unicorn shop is well-known for its eclectic gifts and crafts. Woodstock Hops N Barley sells a wide selection of craft beers.

Woodstock Vermont Shopping | New England | Woodstock Vermont Itinerary
Woodstock Vermont Shopping ur

Walking along the town green, enjoy the Federal-Style and Greek Revival architecture. Take photos by the Middle Covered Bridge. It is always fun to stop into the lovely Woodstock Inn and Resort for lunch in the Red Rooster restaurant or drinks in the tavern.



If you have time, drive to Woodstock’s East End Park and hike the Ottauquechee River Trail. The 3-mile walk runs adjacent to the river past stands of forest, fields, and marshes.


Have dinner in town, we enjoy the Prince and the Pauper Restaurant (but there are many great options!).

Wood Pile | Woodstock Vermont Things To Do | New England Travel
Wood Pile | Woodstock, Vermont

Day 2: Billings Farm Museum, Marsh-Billings-Rockefeller National Historic Park, and Mount Tom

Dress for a day outdoors . Grab a backpack, and drive to Woodstock’s Billings Farm Museum. Located on the edge of town, this outdoor museum depicts Vermont past- and present-day life. The farm’s museum displays are located in a gorgeous barn complex. Exhibits feature farm life in the 19th century. Outside of the museum, visitors tour the farm’s gardens, barns, and pastures. There is a working dairy, and many animals to view onsite.

Pastures | Billings Farm Museum | Woodstock Vermont Weekend | New England Travel
Pastures | Billings Farm Museum

Later in the day, travel across the street to the Marsh-Billings-Rockefeller National Historic Site. The expansive park is a favorite hiking and cross-country skiing destination for locals and travelers. The park offers guided tours of an 1800’s mansion, greenhouse, gardens, and 20-miles of hiking trails.

Marsh Billings Rockefeller National Historic Park | Woodstock Vermont 3 Day Itinerary | New England
Marsh Billings Rockefeller Mansion

For those who feel like vigorous exercise, within the park stands 1359’ Mount Tom. The moderately difficult hike takes in logging trails, ponds, and spectacular views from the summit.

Garden | Woodstock Vt Itinerary | Things to do in Woodstock Vermont | New England
Garden Woodstock Vermont

Day 3: Quechee (Antiques Collaborative, Gorge, Cover Bridge, and Gorge Village)

It’s a day of Quechee! Quechee village lies about 7-miles outside of Woodstock.


Begin your day by driving along scenic Route 4 to the Quechee Antiques Collaborative. The Collaborative is a collection of over 165 dealers displaying their wares in a restored farm house gallery. Wander several floors of country furniture, coins, and housewares.

Quechee Antiques Collaborative | Woodstock Vermont 3 Day Travel Itinerary | New England
Quechee Antiques Collaborative

Next, travel on to Quechee Gorge. The 165’ ravine is located in the town of Hartford. The tourist attraction has a bridge that spans the Ottauquechee River. Tourists can park at either end of the bridge, and walk the sidewalks to view the gorge. Other ways to experience the gorge include by Segway Tour, or by trail through the State Park.

Quechee Gorge | Woodstock Vermont Itinerary | Things to do in Woodstock Vermont
Quechee Gorge

A short distance past Quechee Gorge, visitors will find the Quechee Gorge Village. This fun mall has a number of Vermont-themed stores, restaurants, and attractions. Onsite there is a huge General Store and Toy Museum, a large antique shop, winery, and farm stand. The village is a great place to stock up on maple syrup, Cabot cheese, and souvenirs. The Public House Restaurant onsite offers comfy pub foods and regional favorites.

Antiques Quechee Gorge Village | Woodstock Vt Itinerary | Woodstock Vermont Things To Do | New England
Antiques Quechee Gorge Village

Next, leave Route 4 and drive into the village of Quechee, and the Quechee Covered Bridge. The bridge spans the beautiful Mill Pond Falls. Park the car. Then, walk the bridge and Quechee Falls Park to view the rocks and waterfall. Next, walk to the Simon Pearce Factory Store. After viewing the glassworks showroom, enjoy a meal in a restaurant that overlooks the falls and Quechee Covered Bridge.

General Store | Quechee Gorge Village | Woodstock Vermont 3 Day Travel Itinerary
General Store | Quechee Gorge Village

Hope you enjoyed your Woodstock Vermont weekend, Laura and Randy

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

Vermont Road Trip | Woodstock Vt Itinerary | New England Travel
Vermont Road Trip



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