The Top 5 Peaks in Windsor County
Whether for the view or for the challenge, climbing the mountainous peaks in Windsor 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 Windsor 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 Windsor County for you here — so you can easily add one to your next adventure.
Last updated: October 7, 2025
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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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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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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The Pinnacle is small, named summit on the Appalachian Trail between Pomfret and Woodstock, Vermont. Although you do not get sweeping views or significant elevation gain (the Pinnacle is 2,546 …
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This is a challenging but rewarding trail leading to Mount Ascutney. It's steep and rocky but incredibly scenic at the same time. When you reach the top, you'll be rewarded …
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