We got our start by believing in the transformative power of all-surface exploration. It’s the best way to race, run, ride, and ultimately experience a landscape. This is our first running-specific event and it certainly won’t be our last.
This is not a half marathon. This is not an Ultra. It’s something completely different. Challenge yourself over 15 miles and close to 2,500ft across an all-surface course covering the best of the best in West Windsor, VT.
This event raises funds for both Ascutney Outdoors and Ascutney Trails Association.
Aug 16, 2026
Distance — 5 Miles
Type — Running
09:00
0.00
Aug 16, 2026
Distance — 13.7 Miles
Type — Running
09:00
0.00
Aug 16, 2026
Distance — 15 Miles
Type — Running
09:00
0.00
These values represent the 3-year monthly averages for August in Brownsville.
Learn more about the host city, Brownsville.
Brownsville is the major village of the town of West Windsor, Vermont. It is home to Ascutney Mountain Resort.
Read more launchRead what other athletes have to say about their experience at the The Overland Trail.
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location_on South Londonderry, Vermont, US
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