Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 35 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 weekly trail running race at Catamount Outdoor Family Center in Williston, VT, offering 5 km and 2.5 km courses with adult and youth categories. Races run rain or shine and follow a clear thunder and bib policy.
Two-day trail festival in Vermont offering seven races from a kids trail to a 53.1 km ultra, with on-site lodging and family amenities.
A hilly 5K at the Guilford Fair in Vermont on mixed surfaces with age group prizes, a special prize for the final finisher, and limited event t shirts for early registrants.
Three community races at Springfield Dam include a free kids 0.5 mile, a 1 mile Maniac Mile for ages 10 and up, and a scenic 3.1 mile course with trails, food vendors, and family activities.
Groton Forest Trail Run on September 12, 2026 offers 25K and 12K trail races hosted by Onion River Outdoors, with volunteer incentives including lunch and a hat.
Trail event at Ascutney Outdoors with a timed 3.2 mile 5K and a 1 mile option supporting Lucy Mackenzie Humane Society; dogs welcome.
Obstacle course races at Killington Ski Resort on Sep 19 to 20 2026, featuring Sprint, Beast, Ultra and kids races.
A fall trail race at Merck Forest and Farmland Center featuring an approximately 8.5 mile loop with about 1,800 feet of climbing and two aid stations. A separate 0.75 mile kids loop circles the farm and allows parent participation.
A one day trail challenge over five Vermont mountains covering about 26 miles and 6142 ft of ascent, with staffed aid stations and limited participant slots.
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 at Shaw Outdoor Center Northfield VT on Sep 27 2026 featuring a Paine Summit 7+ mile and a 6k Anchor Challenge with a 4-person team option.
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 10 km trail race on October 3, 2026 in Lake Elmore, Vermont, held on trails in Elmore State Park with entry fees from USD 35.30 to USD 56.50.
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.
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.