The Top 20 Attractions in Windsor County
There are plenty of places to see and visit in Windsor County. Whether you love hiking or cycling, Windsor County is a region where 20
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: October 12, 2025
The Pogue is a small, round, man-made pond with trails that circumnavigate it, located in Woodstock, Vermont, in the Marsh-Billings-Rockefeller National Historical Park. Be aware that there is no fishing …
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The Quechee Gorge Bridge overlooks the Quechee Gorge, which is also known as "Vermont's little Grand Canyon." This deep, mile-long chasm was formed during the Ice Age, by the melting …
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Mount Tom stands at 1,357 in Woodstock, Vermont and is part of the Marsh-Billings-Rockefeller National Historical Park. From the summit you get fantastic views of the town of Woodstock and …
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The Carriage Barn Visitor Center is open from 10am-5pm, Memorial Day weekend until October 31. The building was constructed on the foundation of a stable that the Billings Family originally …
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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 …
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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 …
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Trails from all directions lead to the summit of Mount Ascutney. There's a lookout tower that takes you above the trees for great views.
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The Crystal Cascade Falls are an 84-foot tall set of cascades on the southwestern aspect of Mount Ascutney. The falls are tucked deep in the woods and aren't visited nearly as much as the summit of the mountain is.
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A short skip and a jump from the summit/observation tower, this area provides a stunning view west over Vermont of Killington, Pico, and Okemo. You may also get lucky and …
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It is worth taking the Old Connecticut River Road to pass through the riverside rural idyll. There are great views of the river all along its length, and a sense of space and calm.
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