Vermont
Vermont Trail Running Calendar 2026-2027
Explore the best trail runs in Vermont for 2026-2027! Our updated list features 26 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.
A family-friendly 5K walk or run at Billings Farm & Museum in Woodstock, VT with live music, cider donuts at the finish, prizes, and museum admission included.
A fundraiser at the Winston Prouty Center on October 10, 2026 featuring a 5K trail run, a half-mile Little Leaf Dash for children, family activities, prizes, and childcare.
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.
Experience a trail marathon or half marathon through the autumn foliage of Vermont featuring 1900 feet of elevation gain per loop and a summit scramble on Round Top Mountain.
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.
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
Trail ultramarathon at Riverside Farm in Pittsfield VT offering distances from 10 miles to 200 miles through Green Mountain terrain.
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.