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Trail Running Calendar near Cambridge 2026-2027

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Explore the top trail runs near Cambridge for 2026-2027! We've gathered 10 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Inaugural Cirque Series at Jay Peak on September 26, 2026 is a trail race with a 7.1 mile course and 3,044 feet of vertical gain across Sport, Expert and Pro divisions.
Bike, run, or walk on the Lamoille Valley Rail Trail in Morrisville, Vermont. Proceeds support services for healthy aging in Central Vermont including groceries, emergency fuel, prescription assistance, and exercise classes.
A 3.1-mile race at Shelburne Farms on 09/27/2026 with a course that mixes gravel paths (not loose), wooded trails, fields and dirt roads. Field limited to 200 racers; registration through Racevermont.com includes a finishers medal.
October 2026
A community-focused 10 km mountain trail race in Lake Elmore, VT with about 1,500 feet of climbing, a post-race taco party and a raffle.
Dog friendly 5K and 10K trail runs at Bolton Valley Resort in Vermont on October 3, 2026, with mixed mountain and ski trails and on course medical support.
Trail marathon and half marathon on October 17, 2026 in Stowe, VT, featuring a 13.1 mile loop with steep climbs and single track.
An uphill run at Stowe Mountain Resort hosted by the Mansfield Nordic Pro Team on June 21 and October 18, 2026. The 1.7 miles course climbs from Midway Lodge to Cliff House and raises funds for the pro team.
A Halloween themed 5K trail race at Arrowhead Golf Course in Milton VT on October 25, 2026. Pre registration fee is $15 and the event is open to runners 12 and older with awards for top male, female, and non binary finishers.
36 hour trail festival at Catamount Outdoor Family Center in Williston, VT, with repeatable three and four mile loops and donation based entry; proceeds split between Catamount and Migrant Justice.
November 2026
A Thanksgiving morning run/walk on the Cambridge Greenway Trail with 3.1 and 1.2 mile options; proceeds support Cambridge Recreation programs.
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