Maine
Maine Trail Running Calendar 2026-2027
Explore the best trail runs in Maine for 2026-2027! Our updated list features 23 exciting trail runs across the region. Find your next trail run in Maine below and join the trail community at these great events!
November 2026
Coastal trail event in Cutler, ME offering a 50K ultra and a 10.5 mile fun run on a rugged figure eight course with mandatory safety gear and live tracking.
A four-hour community hill-climb fundraiser at Powderhouse Hill in South Berwick on November 21, 2026, supporting the Marshwood High School Ski Team with music, BBQ, and raffles.
December 2026
A moonlit snowshoe or skin climb up Tote Road to Bullwinkle's, about 2 mi round trip, with a minimum donation and treats and hot beverages at the summit.
January 2027
A winter trail 5 Miler at Bradbury Mountain in Pownal, ME, on mixed single and double track trails with variable winter conditions and a 125 runner cap.
February 2027
A ski endurance event at Black Mountain of Maine the weekend of February 5, 2027, with laps on the Allagash trail, mandatory helmets, aid stations, and category awards.
March 2027
A 5K run from downtown Greenville across frozen Moosehead Lake toward the Mile Light on March 13, 2027 with a post race chili lunch.
May 2027
Two day trail running festival at Pineland Farms in New Gloucester ME on May 29 and 30 2027 with long runs Saturday, short runs Sunday and dog friendly events.
June 2027
A fast, slightly rowdy 6 mile trail race at Bradbury Mountain State Park in Pownal, ME, organized by Trail Monster Running as part of the Bradbury Mountain Trail Race Series.
July 2027
Eat a whoopie every quarter mile while running timed solo, relay, or endurance laps on a short campus loop in Bar Harbor.
Run an approximately 4.16 mile loop around Portland's Back Cove each hour until one runner remains, with two aid stations and onsite support at Back Cove Park.
A 9 mile two lap trail race on Bradbury Mountain State Park single track in Pownal ME organized by Trail Monster Running and capped at 140 runners.
A 5K obstacle course at Sunday River Resort in Newry, Maine, featuring ski-trail and wooded terrain with custom built obstacles.
August 2027
Multi-distance trail event on Blue Hill Mountain (Blue Hill, ME) with 5k, 10k, 25k and 50k looped courses, aid stations, and proceeds to local trusts.
A twisting single track trail race in Pownal ME, about 12 miles long, with a 3 hour 36 minute cutoff and a 140 runner field limit.
Trail races in Windham ME offering 50K, marathon and 13M on technical single-track loops with two aid stations and custom finisher swag.
September 2027
Backyard ultra race on a 4.2 mile wooded loop in New Gloucester, Maine, with double track, moderate elevation gain, and a $150 registration fee.
Three trail races in Camden Hills State Park in September 2027 including a 50K, 20k and 10K across rocky, forested trails with significant elevation and aid stations.
A community 5K on September 12, 2027 in Arundel, ME supporting local children and elders; entry includes a complimentary T-shirt and medallion.
Trail races in Pownal, ME on September 12, 2027 offering a 25K single lap that counts for the series and a capped 50K two-lap option on technical singletrack.
October 2027
A 5k trail run and 1 mile walk at Peace Ridge Sanctuary in October, raising funds for rescued animals with yoga, vegan BBQ, family activities, and a virtual option.