Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 28 exciting trail runs across the region. Find your next trail run in Vermont below and join the trail community at these great events!
October 2026
Experience a rugged ultra marathon on Wrights Mountain in Vermont featuring a 10K loop with 1600 feet of climbing during the peak foliage season.
Family-friendly 5K at Billings Farm in Woodstock with live music, cider donuts at the finish, and prizes for top finishers and best costumes.
A fall fundraiser featuring a forested 5K and a half-mile Little Leaf Dash with family activities, prizes, a raffle, and on-site refreshments.
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.
Trail half and full marathon at Trapp Family Lodge in Vermont, featuring winding single track, a climb to Round Top, and about 3800 ft total elevation for the full distance.
Uphill mountain run at Stowe Mountain Resort on June 21 and October 18, 2026 hosted by the Mansfield Nordic Pro Team with proceeds supporting the pro team.
Family friendly Halloween 5k at Rock Point School in Burlington supporting COTS; $15 registration with proceeds aiding services for people experiencing homelessness.
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.
Sixth annual RutFest is a 36 hour community trail festival in Williston, VT with repeating 3 and 4 mile loops, donation based entry, and proceeds split between Catamount and Migrant Justice.
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.
December 2026
Nighttime 5K in Morrisville, VT along the Lamoille Valley Rail Trail with required headlamps and a riverside finish party featuring s'mores, hot cocoa, music, and awards.
February 2027
A multi-day winter endurance race in Pittsfield, VT with snow terrain, physical obstacles and unknown start and end times; entry is by application only.
A historic ski race from Mt. Mansfield to Stowe Village with 6 km and 20 km divisions in classic, skate, and fixed heel formats.
May 2027
A multi-distance trail ultra at Riverside Farm in Pittsfield, Vermont featuring 10M to 200M options, mandatory headlamps for longer distances, drop bag support, and on-course aid stations.
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 72-hour application-only endurance obstacle race held June 23–26, 2027 at Riverside Farm in Pittsfield, VT, with team options and a GOVX service-member discount.
A three-stage Hurricane Heat endurance event at Riverside Farm in Pittsfield VT offering 4 hour, 12 hour, and 24 hour options with tickets from USD 79.
An endurance event at Riverside Farm in Pittsfield VT offering a 24 Hour Challenge and a Last Spartan Standing format with 45 minute loop intervals and 970 feet of gain per loop.