The Top 9 Attractions around Windsor
There are plenty of places to see and visit around Windsor. Whether you love hiking or cycling, Windsor is a region where 9
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: November 4, 2025
Observation Tower on Mount Ascutney
Highlight • Monument
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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Crystal Cascade Falls
Highlight • Waterfall
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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West Peak Vista / Glider Area on Mt. Ascutney
Highlight • Viewpoint
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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Saint-Gaudens National Historical Park
Highlight • Historical Site
The road cuts through the Saint-Gaudens Historical National Park. It was once the home of the celebrated sculptor, Augustus Saint-Gaudens. The grounds are peppered with casts of his most famous …
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Cornish-Windsor Covered Bridge
Highlight • Bridge
The Cornish-Windsor Bridge was built in 1866 and is the longest wooden covered bridge in the country. It's an iconic way to cross the Connecticut River and travel between New …
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