Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 34 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
A fall variant of Craftsbury's Tuesday Night Trail Races with an earlier-season start, fewer events, and running-only format with no bicycle entries.
A one-day mountain trail challenge over five peaks around Westmore, about 26 miles and 6,142 feet of ascent with staffed aid stations and shuttle support.
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.
A multi-discipline endurance weekend at Ascutney Outdoors with 50 mile and 50K run options, relays, mountain bike races, and kids events, benefiting 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.
Experience the Anchor Challenge at Norwich University with a summit trail run or a 6k team race on the scenic Paine Mountain trail system.
October 2026
Community 10 km mountain trail run in Lake Elmore, VT with about 1,500 ft of climbing, a post race taco party and a raffle supporting local backcountry recreation.
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.
Experience a rugged ultra marathon on Wrights Mountain in Vermont featuring a 10K loop with 1600 feet of climbing during the peak foliage season.
A family friendly 5K walk or run at Billings Farm & Museum in Woodstock VT with live music, a cider donut at the finish, and awards for top finishers and best costumes.
A fundraising event in Brattleboro with a 5K trail run and a half‑mile Little Leaf Dash for children, plus fall activities and family amenities.
A 5K technical trail run at the Chris Lewit Tennis Academy in South Londonderry, Vermont, through wooded laps by the West River with proceeds benefiting veterans charities.
Fundraising running event in Ripton with in person and virtual 5K and 10.4K options, a kids race, and proceeds benefiting Ripton students.
Experience a trail marathon or half marathon through the autumn foliage of Vermont featuring 1900 feet of elevation gain per loop and a summit scramble on Round Top Mountain.
Uphill mountain run at Stowe Mountain Resort on June 21 and October 18, 2026, hosted by Mansfield Nordic Pro Team with proceeds supporting the pro athletes.
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.
RutFest is a 36 hour community trail event at Catamount Outdoor Family Center in Williston, VT with repeatable 3 and 4 mile loops and donation based entry supporting local causes.
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.
A Thanksgiving morning run/walk on the Cambridge Greenway Trail with 3.1 and 1.2 mile options; proceeds support Cambridge Recreation programs.