Overview
Windsor is in Southern Vermont. Windsor sits on the banks of the Connecticut River. Mount Ascutney, one of Vermont's only volcanoes (inactive), offers great views while visiting this small but progressive community.
4 sights · 2 things to do · 6 places to eat · 1 bars & cafés · 3 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Windsor
Ascutney State Park
Wilgus State Park
Popular with canoeists or hikers. Has many acres of forest and trails as well as Evarts pond. There is also a cabin/lean-to for larger functions. These areas can be accessed year round.
Old Constitution House
American Precision Museum
Windsor is the home of interchangeable parts.
Vermont State Prison
The former was built in 1820 and was closed in 1975. At the time of closure it was the oldest prison in the United States.
John P. Larkin Country Club
9 holes. During the winter a great place to go sledding with the family.
Plan your trip
Best time to visit & weather
Most comfortable: May–Sep. Summer highs reach about 83°F; winter lows dip to about 13°F. Cold months (Jan, Feb, Dec) can bring snow and ice; check road conditions. Wettest: Jul and Oct. (climate data from nearby Hanover)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- LEB Lebanon Municipal Airport, Lebanon — 11 mi away. Directions
- RUT Rutland - Southern Vermont Regional Airport, Rutland — 29 mi away. Directions
- ALB Albany International Airport, Albany — 88 mi away (major hub). Directions
Interstate 91 passes through Windsor. Windsor is approximately 12 miles south from the Upper Valley tri-towns of Hanover and Lebanon, NH and Hartford, VT.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 2-day itinerary
Day 1
- Morning Ascutney State Park, Wilgus State Park
- Lunch Windsor Station Restaurant & Barroom
- Afternoon Old Constitution House
- Dinner Pizza Chef
- Evening Harpoon Brewery
Day 2
- Morning American Precision Museum, Vermont State Prison
- Lunch Boston Dreams
- Afternoon John P. Larkin Country Club
- Dinner The Windsor Diner
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
Founded in 1761, the town of Windsor boasts historical significance in that the Republic of Vermont was written there. The Old Constitution House is preserved as the specific building in which the document was drafted. There are many sites of historical importance within the community.
The industry in the area is rich and varied; Simon Pearce, the renowned producer of blown glass and hand-thrown pottery, is but one of the renowned businesses within the community. There are also many small and locally owned retail shops that offer antiques, books, crafts, wines, gifts, and clothing. The many restaurants offer various cuisine and the recreation is plentiful. Windsor is also just a short drive away from Woodstock.
Get in
By car
Interstate 91 passes through Windsor. Windsor is approximately 12 miles south from the Upper Valley tri-towns of Hanover and Lebanon, NH and Hartford, VT.
By train
Windsor is served by Amtrak via its Vermonter train between Washington, D.C. and St. Albans. Southbound trains arrive around noon while northbound arrives just before 6PM. Windsor-Mt. Ascutney station is centrally located at 26 Depot Ave. There are no amenities, but the old station has been converted to a restaurant.
Get around
A car is preferable in this rural area, however biking is common in the warmer months.
See
Windsor is a very historical town with many 18th-century buildings that are in various stages of rehabilitation. Windsor was the site of the writing of the Constitution of the Republic of Vermont. Vermont was never a colony of England and had been claimed land by New Hampshire and New York State. Ethan Allen and the Green Mountain Boys fought these states and formed their own republic on July 7, 1777, by signing a constitution that was the first to allow women rights and ban slavery. Vermont remained a republic for 14 years when it was recognized by the United States and became the 14th state. The Constitution house, located on Route 5 North heading into town, has been restored and is open to the public. This historic building has moved from its original location to where it sits today. Another historic building in this town is the Toll House; this is where tolls were collected after crossing the Covered Bridge over the Connecticut River.
There are two pristine ponds that are public owned. Windsor also is home to the oldest continually operating post office in the same location in America, and one of the longest covered bridges in America.
See Old Constitution House
See Vermont State Prison
The former was built in 1820 and was closed in 1975. At the time of closure it was the oldest prison in the United States.
Do
Windsor is a town with something to do for everyone to do. Vermont's fall months there are foliage viewing; the spring brings mud season and maple sugaring. In Windsor there are scenes of small town life with plenty of trees, flowers and shrubs and is more rural as you travel further from downtown.
Windsor is a great place to go outdoors. You can walk virtually anywhere, including the mile square around the downtown area. You can also bike down many types of roads from cement to dirt, and flat to hills. Windsor is also home to Paradise Park, a great local wooded area with plenty of open spaces, streams, and a pond.
Do John P. Larkin Country Club (Country Club)
9 holes. During the winter a great place to go sledding with the family.
Buy
Windsor is home to many shops and convenience stores. The smaller businesses include Simon Pearce glass blowing studio. Larger chain stores on the north end of town include Price Chopper, Aubuchon Hardware, and Dollar General.
Eat
Eat Pizza Chef
The Pizza Chef has pizza, grinders, spaghetti,Italian dinners, salads, and side dinners.
Eat Boston Dreams
Sports art & memorabilia, Wifi & comfortable seating. Food: coffee, tea, espresso, hot chocolate, ice cream, smoothies, shakes, freshly baked goods.
Eat Windsor Station Restaurant & Barroom
Drink
Drink Harpoon Brewery
Great bar as well as a family restaurant; Harpoon makes beer on site.
Sleep
Camping
Stay Ascutney State Park
Has 39 wooded tent or trailer sites and 10 lean-to sites inside two camp loops. Each loop has a rest room providing modern plumbing and hot showers (fee). Sanitary dump station for RVs, but no hookups. There is a small picnic area at the foot of the summit, and a shelter/picnic area midway up.
Stay Wilgus State Park
I-91, Exit #8 Go 1-1/2 mi S on US Rt 5. There are 2 cabins, 19 tent sites and 6 lean-to sites which are located along the Connecticut River bank. Rest room with running water and hot showers (fee). Picnic area with 3 lean-tos in the group area. Canoe and kayak are available. A trailer sanitary station is located by the ranger's quarters.
Go next
The neighboring Cornish, New Hampshire, which is just across the covered bridge, is home to the Saint-Gaudens National Historical Park, which preserves the home and studio of sculptor Augustus Saint-Gaudens (1848-1907).
Nearby
Cornish
City / town · 6 listings · 1 mi away
Brownsville
City / town · 1 listings · 4 mi away
Claremont
City / town · 4 listings · 7 mi away
Quechee
City / town · 4 listings · 12 mi away
Woodstock
City / town · 16 listings · 12 mi away
White River Junction
City / town · 15 listings · 12 mi away
Lebanon
City / town · 3 listings · 13 mi away
Springfield
City / town · 11 listings · 14 mi away
My experience
Write about your trip here. Notes save automatically in this browser as you type; back them up from My journal.