Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 36 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 family-focused event at Springfield Dam on September 12, 2026 featuring a free kids half mile, a one mile Maniac Mile, a scenic 5K, and a Family Fun Zone.
Groton Forest Trail Run on September 12, 2026 offers 25K and 12K trail courses hosted by Onion River Outdoors; volunteers receive lunch, a neon ORO hat and a future race entry.
Trail event at Ascutney Outdoors with a timed 3.2 mile 5K and a 1 mile option supporting Lucy Mackenzie Humane Society; dogs welcome.
A two day Spartan obstacle race weekend at Killington Ski Resort featuring Sprint, Beast, Ultra and kids races on steep, off trail mountain terrain.
Trail race at Merck Forest & Farmland Center with an 8.5 mile loop of about 1,800 ft climbing and a 0.75 mile kids farm loop.
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.
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
Fourth annual CLTA 5K honors a Purple Heart recipient and USAF Major General with a trail course through fall foliage near Manchester, Vermont.
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 event on a 10K loop at Wright's Mountain in Bradford, VT offering 30 hour, 12 hour and 10K options with a 100-runner cap and themed tarot awards.
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 fundraiser featuring a 5K trail run and a half mile Little Leaf Dash through the Winston Prouty campus forest and fields with family activities.
Fundraising running event in Ripton with in person and virtual 5K and 10.4K options, a kids race, and proceeds benefiting Ripton students.
Trail marathon and half marathon on October 17, 2026 in Stowe, VT, featuring a 13.1 mile loop with steep climbs and single track.