Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 37 exciting trail runs across the region. Find your next trail run in Vermont below and join the trail community at these great events!
September 2026
Trail racing at Jay Peak on 09/26/2026 covering 7.1 miles with 3,044 feet of vertical gain, multiple competition divisions, timing with disposable bib chips, aid station hydration, race prizes and points toward 2026 season standings.
Mountain bike and ultra-run event at Ascutney Outdoors near West Windsor VT with 50 mile and 50K options, relays and kids races, benefits Vermont Adaptive.
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 at Paine Mountain in Northfield VT featuring a 7.5 mile summit course, a 6K Anchor route, and free youth races supporting local trail management and XC programs.
October 2026
Trail event in Bradford Vermont with looped mountain course, 30 hour, 12 hour and 6 mile options, tarot themed awards and a 100 runner cap.
Trail marathon and half marathon at Trapp Family Lodge in Stowe, VT on October 17, 2026, run on 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.
November 2026
A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.
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.
June 2027
A multi-day trail ultramarathon in Pittsfield, Vermont featuring distances from 10 miles to 200 miles on Green Mountain trails with mandatory headlamps for the longest events.
July 2027
A marked 5k trail run and walk on July 4 in Rochester starting and finishing at River Brook Park, following single-track trails through Chantrea Field and the VCR Connector.
Trail relay held in July at Ascutney Outdoor Center in Brownsville VT featuring multi-runner team divisions, single track trails, camping and glamping options.
July ultramarathon in Vermont offering 100 mile and 100 kilometer options, 17,000 feet of climbing, with proceeds supporting Vermont Adaptive Ski and Sport.
A last runner and rucker standing event on a 1 mile loop at Northeast Slopes in Corinth VT, with weighted rucking rules and memorial loops honoring members of 2/4 Marines.