Bolton
Trail Running Calendar near Bolton 2026-2027
Explore the top trail runs near Bolton for 2026-2027! We've gathered 13 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
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.
Trail races on Paine Mountain in Northfield, VT with a 7.5 mile summit course, a 6K Anchor Challenge, and free youth races.
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.
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.
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.
May 2027
A multi day trail running festival in Ripton, Vermont featuring races from a 9 mile course up to multi day marathon series and ultra distances. Held at Silver Towers Camp in Green Mountain National Forest with on site camping for a small fee.