The town of Windsor in the picturesque state of Vermont benefits from one of New England’s most beautiful locations. Situated by the Connecticut River under the scenic Mount Ascutney, it’s a place where scenic natural beauty meets history. Unique shopping experiences, a charming downtown district, outdoor recreation opportunities, and more attract numerous visitors every year. In addition to a quaint Historic District full of architectural history, one of the largest in the state, Windsor is also home to many artisans that can be seen at work and America’s longest two-span covered bridge. Hours/availability may have changed.

1.Cornish-Windsor Covered Bridge

Cornish-Windsor Covered Bridge
© World Travel Photos/

With more than one hundred charming covered bridges, it can be hard to choose which one to visit in Vermont. If travelers are going to see just one, perhaps the best to see is the Cornish-Windsor Covered Bridge. At approximately 449 feet in length, it’s the country’s longest wooden covered bridge, stretching across the Connecticut River and connecting New Hampshire and Vermont. While this particular version of the beautiful and historic Cornish-Windsor Covered Bridge was built in 1866, three bridges have stood at the site, with the first one dating all the way back to the year 1796.

Windsor, VT

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2.Harpoon Brewery, Windsor, Vermont

Harpoon Brewery, Windsor, Vermont
© Harpoon Brewery

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. They also shared a desire for more flavorful, better options of beer. Eventually, a second Harpoon Brewery was established in the town of Windsor, Vermont in order to keep up with the increasing demand for UFO and Harpoon beers. Beer lovers can visit the Harpoon Riverbend Taps and Beer Garden while in Windsor and sip on a selection of craft brews, seltzers, and ciders, as well as a variety of tasty food.

336 Ruth Carney Drive, Windsor, VT 05089, Phone: 802-674-5491

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3.Mount Ascutney, Windsor, Vermont

Mount Ascutney, Windsor, Vermont
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Mount Ascutney is Windsor County’s second highest peak and is a popular place in Windsor, Vermont for outdoor recreational activities. The park features four different trailheads with over a dozen miles of trails for hiking. These trails lead visitors to a variety of sites of days gone by, such as relics of logging operations, homesteads, and quarries. There are also a number of amazing viewpoints with vistas of the state’s scenic Connecticut River Valley, as well as an observation tower located at the summit of Mount Ascutney. Hang gliding and camping are also popular activities at the park.

1826 Back Mountain Rd, Windsor, VT 05089, Phone: 802-674-2060

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4.Great River Outfitters and Path of Life Garden

Great River Outfitters and Path of Life Garden
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The Great River Outfitters and Path of Life Garden in the town of Windsor are two companies working in tandem. Great River Outfitters provides access for both visitors and tourists alike to a wide array of outdoor activities. Operating year-round, they offer trips for people of all skill levels, ranging from beginner to advanced. The Path of Life Garden is a beautiful Japanese-inspired garden spanning across more than a dozen acres behind the Great River Outfitters, telling the story of “the circle of life.” Trails wind their way through the grounds and Deluxe Tent camping is available in the garden.

6 Park Rd, Windsor, VT 05089, Phone: 802-674-9933

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5.American Precision Museum, Windsor, Vermont

American Precision Museum, Windsor, Vermont
© 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 the effect the work has had on everyday life. Housed within the original Robbins and Lawrence Armory dating back to 1846, the museum today is home to the country’s largest collection of “historically significant machine tools.” Exhibits share the stories of the people who made and used machine tools. The American Precision Museum is open seven days a week from 10:00am until 5:00pm, from Memorial Day weekend to the end of October.

196 Main St, Windsor, VT 05089, Phone: 802-674-5781

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6.Old Constitution House, Windsor, Vermont

Old Constitution House, Windsor, Vermont
© Old Constitution House

The Old Constitution House in the town of Windsor, Vermont is a state historic site often referred to as “the Birthplace of Vermont.” The historical building is the place where delegates of the Republic of Vermont came together to write a constitution. This Vermont constitution was the first constitution in America to authorize a public school system, allow men without property ownership to vote, and to prohibit slavery. One of the stops along the Vermont African American Heritage Trail, the Old Constitution House is open on Saturdays and Sundays from the end of May through the middle of October.

16 Main St, Windsor, VT 05089, Phone: 802-674-6628

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7.Braeburn Siberians, Windsor, Vermont

Braeburn Siberians, Windsor, Vermont
© Braeburn Siberians

The Braeburn Siberians of Windsor, Vermont offers a hands-on, thrilling, and unique outdoor experience for visitors and locals alike. A great adventure for people of all ages who love dogs, the dog sledding excursions available with Braeburn Siberians gives people an escape from hectic everyday life and a chance to experience dog sledding without having to travel to Alaska. While the kennel is based in Windsor, the dog sledding trips take place in Claremont, New Hampshire across the Connecticut River. Trails run through pristine woodlands and fields, as well as along rivers, often offering amazing views along the way.

Windsor, VT, Phone: 802-738-8337

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8.Old South Church, Windsor, Vermont

Old South Church, Windsor, Vermont
© Old South Church

The Old South Church in the historic town of Windsor was originally founded back in the year 1768, however, the present church was designed by Asher Benjamin and built thirty years later in 1798. Nationally affiliated with the United Church of Christ, the Old South Church celebrated its 250 years as an important part of the local community in 2018. The town itself was charted in 1761 and the history of both the church and town have also been intertwined. With the exception of a front portico that was added in 1920, the church exterior has not been changed since 1798.

146 Main St, Windsor, VT 05089, Phone: 802-674-5087

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9.The Windsor Station Restaurant and Barroom, Windsor, VT

The Windsor Station Restaurant and Barroom, Windsor, VT
© The Windsor Station Restaurant and Barroom

The Windsor Station Restaurant and Barroom is a classic neighborhood eatery that features numerous spirits, wines, and foods that are locally produced. Housed within a historic train station in WIndsor, Vermont, 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. The Windsor Station Restaurant is open Wednesday to Saturday from 4:00pm until 9:00pm and on Sundays from 4:00pm until 8:00pm. Live music can often be heard at night at the Windsor Station Restaurant as well.

26 Depot Ave, Windsor, VT 05089, Phone: 802-674-4180

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9 Best Things to Do in Windsor, Vermont

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