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
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.
An 18 mile trail run around Victory Hill, Vermont with about 2500 ft of climbing, refreshments, merchandise sales, volunteer hand timing and free camping.
November 2026
A spooky themed 5k trail fun run and walk on the West River Trail in Londonderry on Nov 1; costumes are encouraged.
Trail running at Hard'ack recreation area in St Albans on November 1, 2026, with 3k and 5k options, changing courses, post-race refreshments and a raffle.
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 along a lit rail trail with required headlamps, winter trail conditions, a riverside finish party, and age group 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.
Historic Stowe Derby features 6 km and 20 km ski races from Mt. Mansfield to Stowe Village with classic, skate, and fixed heel divisions.
April 2027
A 50K trail race at Saskadena Six in South Pomfret, VT on April 10, 2027, featuring hilly dirt roads, 3,726 ft of gain, variable weather, and an 8 hour cutoff.
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.
Cirque Series at Killington is an 8.2 mile trail race with 3,010 feet of vertical gain, featuring Sport, Expert and Pro divisions and gear and cash prizes.
A trail ultramarathon in Stowe VT on June 26, 2027, featuring a 25K loop and a 50K option of two laps around Trapp Family Lodge trails.
July 2027
A marked 5k trail run and walk on July 4 in Rochester starting and finishing at River Brook Park, following single-track trails through Chantrea Field and the VCR Connector.