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!
August 2026
A weekly trail race series in Williston, VT offering 5 km and 2.5 km options with adult and youth categories, bib pickup and on-course water refill. Events run rain or shine and follow a posted thunder and cancellation policy.
Public 5K cross country invitational at Tree Farm Recreational Facility, Essex Junction, VT on Aug 29, 2026 for middle and high school athletes, coaches and families.
A 10 km loop in Perkinsville VT on trails and dirt roads with a shallow river crossing, a nearby swimming hole, and proceeds supporting Springfield High School Cross Country.
Late-August Stowe fundraiser where runners, hikers and cyclists climb Mt. Mansfield via the 4.3-mile Mansfield Toll Road to benefit the Catamount Trail Association.
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.
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 fundraiser at Ascutney Outdoors with a timed 3.2 mile 5K and a 1 mile option, dogs welcome on leash, supporting Lucy Mackenzie Humane Society 111th anniversary.
A weekend of mountain obstacle races at Killington Ski Resort with Sprint, Beast, Ultra, kids races, and spectator access on September 19–20, 2026.
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.
A 7.1 mile trail race at Jay Peak with 3,044 feet of climb, multiple divisions, gear and cash prizes, disposable timing chips, and a 500 runner cap.
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 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.
Trail event in Bradford Vermont with 30 hour, 12 hour and 10K options on a 10K loop and awards that include tarot cards and a buckle for 100 miles.