The Top 5 Peaks in Windham County
Whether for the view or for the challenge, climbing the mountainous peaks in Windham County is the best way to experience more of this beautiful region. But with 5
to choose from, it can be tough to know which peak to proceed with. That’s why we’ve collected the best peaks and summits in Windham County for you here — so you can easily add one to your next adventure.
to choose from, it can be tough to know which peak to proceed with. That’s why we’ve collected the best peaks and summits in Windham County for you here — so you can easily add one to your next adventure.
Last updated: October 13, 2025
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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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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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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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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The Putney Mountain area is offering more than 800 acres of conserved land along with around 15 miles of hiking trails along the Windmill Hill Ridgeline.
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