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
Community 10 km mountain trail run in Lake Elmore, VT with about 1,500 ft of climbing, a post race taco party and a raffle supporting local backcountry recreation.
Dog friendly 5K and 10K trail runs at Bolton Valley Resort in Vermont on October 3, 2026, with mixed mountain and ski trails and on course medical support.
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, a cider donut at the finish, and awards for top finishers and best costumes.
A fundraising event in Brattleboro with a 5K trail run and a half‑mile Little Leaf Dash for children, plus fall activities and family amenities.
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 Mansfield Nordic Pro Team with proceeds supporting the pro athletes.
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.
RutFest is a 36 hour community trail event at Catamount Outdoor Family Center in Williston, VT with repeatable 3 and 4 mile loops and donation based entry supporting local causes.
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
Multi day winter endurance race in Pittsfield, Vermont (Feb 18 to 20, 2027) on snow covered terrain; entry requires application and acceptance to receive a ticket code.
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 endurance obstacle course event in Pittsfield, Vermont from June 23 to 26, 2027, requiring prior application and acceptance for ticket access.
A three stage Hurricane Heat endurance event at Riverside Farm near Pittsfield, VT offering 4 hour, 12 hour, and 24 hour options with 40 plus challenges and age 18 plus.