Looking for New England charm with history and mountain beauty? Head to Windsor, Vermont! Known as the Birthplace of Vermont, this quaint town blends colonial heritage, scenic landscapes, and artisan culture. Whether you're strolling covered bridges or sipping local spirits, Windsor offers a peaceful and authentic Vermont escape.

Best Time to Visit

The best time to visit Windsor is during autumn (late September to mid-October) for spectacular foliage or summer (June–August) for outdoor activities and festivals. Winter brings cozy charm and snow-covered scenery, while spring sees maple tapping and quiet trails.

How to Get There

  • By Car: Located along I-91 and U.S. Route 5, Windsor is about 2.5 hours from Boston and 1 hour from Montpelier.
  • By Air: The nearest airport is Lebanon Municipal Airport (LEB), 30 minutes away, or Burlington International Airport (BTV), about 1.5 hours away.
  • By Train: Amtrak’s Vermonter line stops at Windsor-Mt. Ascutney Station, with service between Washington, D.C. and northern Vermont.

Where to Stay

  • The Snapdragon Inn – Elegant boutique inn in a historic home with modern touches and garden views.
  • The Windsor Mansion Inn – Grand hilltop inn with antique décor, breakfast service, and sweeping valley views.
  • Climb Every Mountain Farmstay – Unique rustic lodging with farm animals and mountain tranquility nearby.

Top Attractions

1.Walk Through History (and Two States) on the Cornish-Windsor Covered Bridge

Walk or drive across one of the longest covered bridges in the U.S., connecting Vermont and New Hampshire.

Walk Through History (and Two States) on the Cornish-Windsor Covered Bridge

© World Travel Photos/stock.adobe.com

  • How many covered bridges are in Vermont?
    • With more than one hundred charming covered bridges, it can be hard to choose which one to visit in Vermont.
  • What is the best covered bridge to visit?
  • How long is the Cornish-Windsor Covered Bridge?
    • At approximately 449 feet in length, it’s the country’s longest wooden covered bridge.
  • Where does the bridge connect?
    • Stretching across the Connecticut River, it connects New Hampshire and Vermont.
  • When was the current bridge built?
    • While this particular version of the beautiful and historic Cornish-Windsor Covered Bridge was built in 1866...
  • How many bridges have stood at this site?
    • Three bridges have stood at the site, with the first one dating all the way back to the year 1796.
  • Where is the Cornish-Windsor Covered Bridge located?
    • Windsor, VT.

2.Raise a Pint and Toast Local Flavor at Harpoon Brewery

Raise a Pint and Toast Local Flavor at Harpoon Brewery

© Harpoon Brewery

  • When and where was Harpoon Brewery founded?
    • Originally founded in 1986 in Boston, Massachusetts, the Harpoon Brewery was created by three friends who shared a love of beer and drinking beer together.
  • Why was Harpoon Brewery established?
    • The founders shared a desire for more flavorful, better options of beer.
  • Where is the second Harpoon Brewery located?
    • A second Harpoon Brewery was established in Windsor, Vermont to keep up with the increasing demand for UFO and Harpoon beers.
  • What can visitors experience at Harpoon Brewery in Windsor?
    • Beer lovers can visit the Harpoon Riverbend Taps and Beer Garden in Windsor and sip on a selection of craft brews, seltzers, and ciders, as well as enjoy a variety of tasty food.
  • Where is Harpoon Brewery in Windsor located?
    • 336 Ruth Carney Drive, Windsor, VT 05089, Phone: 802-674-5491

3.Hike or Glide to Sweeping Views from Majestic Mount Ascutney

Hike or drive to panoramic views from this iconic Southern Vermont mountain.

Hike or Glide to Sweeping Views from Majestic Mount Ascutney

© Craig Zerbe/stock.adobe.com

  • What is Mount Ascutney?
    • Mount Ascutney is Windsor County’s second highest peak and a popular destination in Windsor, Vermont for outdoor recreational activities.
  • What hiking opportunities are available at Mount Ascutney?
    • The park features four different trailheads with over a dozen miles of trails for hiking.
  • What historical sites can be seen along the trails?
    • The trails lead visitors to relics of logging operations, homesteads, and quarries.
  • Are there scenic viewpoints at Mount Ascutney?
    • Yes! There are several amazing viewpoints with vistas of Vermont’s scenic Connecticut River Valley.
  • Is there an observation tower?
    • Yes! An observation tower is located at the summit of Mount Ascutney.
  • What other outdoor activities are popular at Mount Ascutney?
    • Hang gliding and camping are also popular activities at the park.
  • Where is Mount Ascutney located?
    • 1826 Back Mountain Rd, Windsor, VT 05089, Phone: 802-674-2060

4.Paddle, Wander, and Reflect with Great River Outfitters and Path of Life Garden

Paddle, Wander, and Reflect with Great River Outfitters and Path of Life Garden

© Tatiana L/stock.adobe.com

  • What are the Great River Outfitters and Path of Life Garden?
  • What services does Great River Outfitters provide?
    • Great River Outfitters provides access for both visitors and tourists to a wide array of outdoor activities.
  • Do they operate year-round?
    • Yes! They operate year-round and offer trips for people of all skill levels, ranging from beginner to advanced.
  • What is the Path of Life Garden?
    • The Path of Life Garden is a beautiful Japanese-inspired garden spanning across more than a dozen acres behind the Great River Outfitters.
  • What does the Path of Life Garden represent?
    • The garden tells the story of “the circle of life.”
  • Are there walking trails?
    • Yes! Trails wind their way through the grounds.
  • Is camping available?
    • Yes! Deluxe Tent camping is available in the garden.
  • Where are they located?
    • 36 Park Rd, Windsor, VT 05089, Phone: 802-674-9933

5.Marvel at the Machines That Built America at the American Precision Museum

Marvel at the Machines That Built America at the American Precision Museum

© American Precision Museum

  • What is the American Precision Museum?
    • The American Precision Museum was established to celebrate the ingenuity of the country’s mechanical forebears, preserve the heritage of mechanical arts, and explore their impact on everyday life.
  • Where is the museum located?
    • The museum is housed within the original Robbins and Lawrence Armory, dating back to 1846.
  • What is unique about the museum’s collection?
    • The museum is home to the country’s largest collection of historically significant machine tools.
  • What do the exhibits showcase?
    • The exhibits share the stories of the people who made and used machine tools.
  • When is the American Precision Museum open?
    • The museum is open seven days a week from 10:00 AM until 5:00 PM, from Memorial Day weekend to the end of October.
  • Where is the museum located?
    • 196 Main St, Windsor, VT 05089, Phone: 802-674-5781

6.Step Into Revolutionary History at the Old Constitution House

Visit the birthplace of Vermont’s constitution, now a museum of state history.

Step Into Revolutionary History at the Old Constitution House

© Old Constitution House

  • What is the Old Constitution House?
    • The Old Constitution House in Windsor, Vermont, is a state historic site often referred to as “the Birthplace of Vermont.”
  • Why is the Old Constitution House historically significant?
    • It is the place where delegates of the Republic of Vermont came together to write a constitution.
  • What made the Vermont Constitution unique?
    • The Vermont Constitution was the first in America to:
      • Authorize a public school system
      • Allow men without property ownership to vote
      • Prohibit slavery
  • Is the Old Constitution House part of any historical trails?
    • Yes! It is one of the stops along the Vermont African American Heritage Trail.
  • When is the Old Constitution House open?
    • The site is open on Saturdays and Sundays from the end of May through the middle of October.
  • Where is the Old Constitution House located?
    • 16 Main St, Windsor, VT 05089, Phone: 802-674-6628

7.Admire Timeless Beauty and Community Spirit at Old South Church

Admire Timeless Beauty and Community Spirit at Old South Church

© Old South Church

  • What is the Old South Church?
    • The Old South Church in the historic town of Windsor was originally founded in 1768.
  • When was the current church building constructed?
    • The present church was designed by Asher Benjamin and built thirty years later in 1798.
  • What is the church’s national affiliation?
    • The Old South Church is nationally affiliated with the United Church of Christ.
  • How long has the Old South Church been part of the community?
    • The church celebrated 250 years as an important part of the local community in 2018.
  • How is the church connected to Windsor’s history?
    • The town itself was chartered in 1761, and the history of both the church and town have been closely intertwined.
  • Has the exterior of the church changed over time?
    • With the exception of a front portico added in 1920, the church exterior has not been changed since 1798.
  • Where is the Old South Church located?
    • 146 Main St, Windsor, VT 05089, Phone: 802-674-5087

Where to Eat

8.If You Love Rustic Charm, Unwind at The Windsor Station Restaurant and Barroom

If You Love Rustic Charm, Unwind at The Windsor Station Restaurant and Barroom

© The Windsor Station Restaurant and Barroom

  • What is the Windsor Station Restaurant and Barroom?
  • Where is the restaurant located?
    • It is housed within a historic train station in Windsor, Vermont.
  • What makes the dining experience unique?
    • The building still has many of its original features, offering guests a step back in time and a whimsical setting for enjoying delicious, fresh Vermont food, cocktails, and craft beer.
  • When is the Windsor Station Restaurant open?
    • The restaurant is open:
      • Wednesday to Saturday from 4:00 PM until 9:00 PM
      • Sundays from 4:00 PM until 8:00 PM
  • Is there live music at the restaurant?
    • Yes! Live music can often be heard at night at the Windsor Station Restaurant.
  • Where is the Windsor Station Restaurant located?
    • 26 Depot Ave, Windsor, VT 05089, Phone: 802-674-4180

Local Events

  • Windsor Farmers Market (June–October) – Weekly event with fresh produce, local crafts, and live music.
  • Harpoon Octoberfest (September) – Annual fall bash at Harpoon Brewery with food, beer, and live bands.
  • Windsor Heritage Days (Summer) – Celebrate local history with reenactments, tours, and community fun.

Day Trips Within 30 Minutes of Windsor, Vermont

  • Woodstock (20–25 min) – Stroll village streets, visit Billings Farm & Museum, or hike to Mount Tom’s summit.
  • Hartland (15–20 min) – Explore forest trails, visit artisan studios, or enjoy peaceful countryside drives.
  • Norwich (25–30 min) – Browse King Arthur Baking’s campus, shop local markets, or walk through charming village streets.
  • Quechee (20–25 min) – Marvel at Quechee Gorge, visit the Vermont Institute of Natural Science, or shop glassblowers and craftspeople.
  • Claremont, NH (10–15 min) – Walk along the Sugar River, visit historic mills, or shop downtown cafés and galleries.
  • White River Junction (25–30 min) – Explore local art spaces, see a play at Northern Stage, or enjoy eclectic dining and bookshops.
  • Springfield (20–25 min) – Visit the Eureka Schoolhouse, explore trails, or enjoy riverside parks and quiet neighborhoods.
  • Plainfield, NH (25–30 min) – Visit the Saint-Gaudens National Historical Park, walk scenic roads, or tour covered bridges.
  • Brownsville (15–20 min) – Hike Ascutney trails, explore small inns and farms, or take in mountain and valley views.

FAQ

  • Where is Windsor located?
    • The town of Windsor is in the picturesque state of Vermont, benefiting from one of New England’s most beautiful locations.
  • What natural features surround Windsor?
    • Situated by the Connecticut River under the scenic Mount Ascutney, Windsor is a place where natural beauty meets history.
  • What attractions bring visitors to Windsor?
    • Visitors are drawn to Windsor for its unique shopping experiences, charming downtown district, and outdoor recreation opportunities.
  • What historic attractions can be found in Windsor?
    • Windsor boasts a quaint Historic District full of architectural history, making it one of the largest in the state.
  • What makes Windsor special for artisans and craftsmanship?
    • Windsor is home to many artisans whose work can be seen throughout the town.
  • What unique bridge can visitors see in Windsor?
    • Windsor is home to America’s longest two-span covered bridge, a must-see landmark.

Plan Your Trip


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