Best attractions and places to see in Windsor County, Vermont, blend historical significance with natural beauty. This region features a diverse landscape, from the Ottauquechee River carving Quechee Gorge to the peaks of Mount Ascutney and Mount Tom. Visitors can explore national historic landmarks, picturesque parks, and vibrant cultural sites. Windsor County offers a rich tapestry of outdoor and cultural experiences for explorers.
Last updated: April 26, 2026
Highlight • Lake
Tip by
Highlight • Bridge
Tip by
Sign up now to discover places like this
Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.
Sign up for free
Highlight • Summit
Tip by
Highlight • Rest Area
Tip by
Highlight • Bridge
Tip by
Highlight • Viewpoint
Tip by
Highlight • Bridge
Translated by Google •
Tip by
Highlight • Lake
Tip by
Highlight • Monument
Tip by
Highlight • Waterfall
Tip by
Sign up for free to discover even more attractions in Windsor County.
Sign up for free
Already have an account?
Start today with a free account
Your next adventure awaits.
Login or Signup
Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.
0
0
Taftsville Covered Bridge was opened in 1836 and is very well maintained. You can also walk down onto the river bank to get a lovely view of the river crossing from below. There are information boards which provide further information about the wooden bridge's history.
0
0
Known as Vermont's Grand Canyon, you get a splendid view of the gorge from the road bridge. You can also park up your bike and take the hiking path to explore it further and go for a swim in the summer.
0
0
Taftsville Covered Bridge was opened in 1836 and is very well maintained. You can also walk down onto the river bank to get a lovely view of the river crossing from below. There are information boards which provide further information about the wooden bridge's history.
1
0
Woodstock Middle Covered Bridge has spanned the Ottauquechee River since 1969 and was supposedly constructed without the use of any nails.
0
0
Little Cascade Falls are a small set of cascades off the side of the Weathersfield Trail. They are often paired with the larger Crystal Cascade Falls at the end of the path.
0
0
Dewey Pond is on the northern end of Quechee State Park and is a fantastic place to hike around and look for birds and other wildlife. Some notable local birds you might see are: yellow-rumped warblers, black- throated warbler Northern goshawks, bald and golden eagles, red-tailed and red-shouldered hawks, ospreys, blue jays, and mourning doves. Deweys Pond was named for A.G. Dewey, who owned a wool mill that operated in the area 1869 until the 1960s and used the water from this pond to operate. You can actually see the remains of the old mill on the main trail.
0
0
Windsor County is rich in history. You can explore the Old Constitution House in Windsor, where Vermont's constitution was signed, or visit the Calvin Coolidge Homestead District in Plymouth Notch, the birthplace of President Calvin Coolidge. The American Precision Museum in Windsor showcases the region's manufacturing heritage. Don't miss the iconic Taftsville Covered Bridge and the Woodstock Middle Covered Bridge, both significant historical landmarks.
Yes, Windsor County offers several family-friendly attractions. The Carriage Barn Visitor Center at Marsh-Billings-Rockefeller National Historical Park is a great starting point. The Montshire Museum of Science in Norwich provides over 150 hands-on exhibits for all ages. You can also enjoy the scenic views from the Quechee Gorge Bridge, often called "Vermont's little Grand Canyon," which is accessible for families.
For breathtaking views, head to the Observation Tower on Mount Ascutney, which offers expansive vistas above the treeline. The Quechee Gorge Bridge provides stunning perspectives of the Ottauquechee River flowing 168 feet below. You can also find beautiful scenery at View from Faulkner Trail on Mount Tom, especially during fall foliage.
Windsor County is perfect for outdoor enthusiasts. You can find numerous hiking trails, such as the Paradise Park Loop or the Greendale Loop Trail. For road cycling, consider routes like the Woodstock Middle Covered Bridge – Taftsville Covered Bridge loop. Running trails are also available, including the Hurricane Forest Wildlife Refuge loop. Explore more options in the Hiking in Windsor County, Road Cycling Routes in Windsor County, and Running Trails in Windsor County guides.
Yes, there are several easy walking options. The Pogue, a 14-acre pond within the Marsh-Billings-Rockefeller National Historical Park, has trails that circumnavigate it, offering a peaceful and accessible walk. Paradise Park in Windsor also features easy and accessible hiking trails around Lake Runnemede. The Quechee Gorge area has paths suitable for a leisurely stroll.
Windsor County boasts a vibrant cultural scene. Artisans Park in Windsor is a hub for local craft foods, beverages, and handmade wares, including Harpoon Brewery and SILO Distillery. You can also visit the Path of Life Sculpture Garden in Windsor, a unique outdoor art park. The Billings Farm & Museum in Woodstock provides insight into Vermont's rural heritage, and the Weston Playhouse Theatre Company offers professional theater productions.
Yes, the iconic Appalachian Trail passes through Windsor County, offering sections for hiking enthusiasts. While specific access points and trail lengths vary, you can find opportunities to experience portions of this famous long-distance hike within the region.
The best time to visit Windsor County for outdoor activities largely depends on your interests. Spring and summer offer lush greenery and pleasant temperatures for hiking, cycling, and exploring. Fall is particularly popular for its spectacular foliage, making it ideal for scenic drives and walks. Winter provides opportunities for snow sports, though some trails may be less accessible.
Absolutely! Windsor County is home to several notable bridges. The Cornish-Windsor Covered Bridge, spanning the Connecticut River, is the longest wooden covered bridge in the United States. You can also visit the Woodstock Middle Covered Bridge, known for reportedly being constructed without nails, and the historic Taftsville Covered Bridge.
Visitors frequently praise the stunning natural beauty, especially the views from the Quechee Gorge Bridge and the expansive vistas from the Observation Tower on Mount Ascutney. The peaceful setting of places like The Pogue and the rich historical significance of sites like the Old Constitution House are also highly appreciated. Many enjoy the blend of outdoor adventure and cultural exploration the region offers.
Beyond the historical sites, Windsor County offers engaging museums. The American Precision Museum in Windsor delves into the history of manufacturing. The Montshire Museum of Science in Norwich provides interactive science exhibits, and the Billings Farm & Museum in Woodstock offers a living history experience of a working farm.
Yes, towns like Woodstock, Quechee, and Windsor, which are central to many attractions, offer a variety of cafes, pubs, and accommodation options. You'll find everything from cozy inns to larger hotels and local eateries serving Vermont fare, ensuring you have convenient choices close to your points of interest.


Are you keen on exploring more awesome places nearby? Browse our guides:
Still not found the Highlight you’re looking for? See guides of the top attractions in other regions: