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Windham County

Windham County

The Top 17 Attractions in Windham County

There are plenty of places to see and visit in Windham County. Whether you love hiking or cycling, Windham County is a region where 17

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: December 9, 2025

Stratton Mountain and fire lookout tower

Highlight • Summit

Stratton Mountain is one of the most iconic peaks on the Long Trail, but not for its height, but rather for its historical significance. It was here in 1909 that …

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Lowell Lake

Highlight • Lake

A lot of activities are possible in this little state park near Londonderry. It includes hiking, non-motorized boating, fishing, picnicking, wildlife watching, as well as winter sports.

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Mount Olga

Highlight • Summit

Mount Olga stands just 2,415 feet (737 m) tall, but still offers grand views over the surrounding landscape — especially if you climb the fire lookout tower at the summit.

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Haystack Mountain

Highlight • Summit

From the top of this mountain you are close to the ski resort "L'Ermitage". You also have exceptional views, especially on the Harriman Reservoir.

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Hamilton Falls

Highlight • Waterfall

This is a wonderful and very picturesque spot. In summer you can enjoy the pool under the waterfall with fresh water ideal for cooling off after the walk.

Remember that …

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Black Mountain

Highlight • Summit

The trees part to make way for outcroppings of stone at the summit which offer great views of the forest and north Brattleboro.

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Black Mountain Trailhead

Highlight • Trail

You can park up off of Rice Farm Road. Parking is limited, but the trail is beautiful and includes many water features.

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Ball Mountain Dam

Highlight • Monument

It is worth reaching the top of the dam. The road in itself is a real pass. When you reach the top the views are amazing, until you get to see Straton Ski Resort

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Livewater Farm

Highlight • Structure

If you’re into cheese, then this is the place. Taylor only makes a couple of cheeses to go with his meats, but he’s legit. Truly artisanal. We talked about milk …

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West River Trail — Spring Tree Road Trailhead

Highlight • Trail

You park near the marina at the southern end of Spring Tree Road in a large gravel lot by the river. From here you follow the river north on the road to where it quickly becomes a bike path.

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Other adventures in Windham County

Roundabout Brattleboro — a charming challenge in the New England countryside

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Cycling in Windham County

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Gravel biking in Windham County

Most popular attractions in Windham County

Mountain Peaks

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Didn’t find what you were looking for?

Are you keen on exploring more awesome places nearby? Browse our guides:

West Brattleboro Chimney Hill Putney Algiers Brattleboro

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Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

Chittenden County Green Mountain And Finger Lakes National Forests Lamoille County Lake Champlain Windsor County Bennington County Washington County Rutland County Addison County Orleans County Grand Isle County Franklin County Caledonia County

The Top 17 Attractions in Windham County

Stratton Mountain and fire lookout tower

Lowell Lake

Mount Olga

Haystack Mountain

Hamilton Falls

Black Mountain

Black Mountain Trailhead

Ball Mountain Dam

Livewater Farm

West River Trail — Spring Tree Road Trailhead

Other adventures in Windham County

Most popular routes in Windham County

Most popular attractions in Windham County

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

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