Maine
Maine Trail Running Calendar 2026-2027
Explore the best trail runs in Maine for 2026-2027! Our updated list features 26 exciting trail runs across the region. Find your next trail run in Maine below and join the trail community at these great events!
October 2026
Trail footraces at Caribou Bog Outdoor Center on 17 Oct 2026 feature a 5ish K and a 6 hour fixed time event with blue and red loop options where laps earn points for individuals and teams.
A community 5K run and walk in Springvale supporting a nonprofit that provides technology to seriously ill children, with awards, kids activities, and a post race barbecue.
A 32.5 mile five lap trail ultra in Windham, ME on Red, Blue and Purple trails with two aid stations per loop and volunteer support.
A trail fundraiser featuring a 6.2 mile summit run to the 1,009 foot peak of Great Pond Mountain and a 1 mile Fun Run to the Dead River.
Community fundraising hike at Lost Valley where participants repeat climbs over a four hour challenge to raise funds for Tree Street Youth.
A community run at Emmons Preserve in Kennebunkport featuring 5K, 10K trail and a kids fun run with medals, music, family activities and a raffle.
A short 2.5 mile community trail run at Thorne Head Preserve in Bath with river views, limited to 150 runners; proceeds support the Kennebec Estuary Land Trust.
A costumed 5K trail run at the Wells Reserve at Laudholm on October 31, 2026 supporting coastal research, with timed results, water stations, awards, and a limited shirt.
Quarry Road Trailfest in Waterville on October 31, 2026 features 5 km and 15 km trail races, a free kids fun run, and post-race awards and festivities.
November 2026
Holiday-themed event in Sanford ME featuring an in-person 5K, a kids Turkey Trot on the stadium track, and a virtual 5K plus a costume contest and raffle.
A coastal single track event in Cutler, Maine featuring a 50K ultra and a 10.5 mile fun run on a figure eight course with mandatory kit checks.
Four hour community hill challenge at Powderhouse Hill in South Berwick, Maine; open format climbs, $35 entry includes long sleeve shirt and post challenge lunch.
December 2026
Organized by volunteers, this free USATF-certified marathon and half in Millinocket, Maine runs a 13.1-mile loop over gravel and pavement; donations support race expenses.
February 2027
Endurance ski event in Rumford, ME with roughly 1.5 mile laps and 1,200 ft climb per lap, mandatory snow helmets and night gear, lodge support and on site aid.
June 2027
A 6 mile trail race in Pownal, ME, part of the Bradbury Mountain series; capped at 140 runners with a 1 hour 48 minute cutoff.
July 2027
Quarter mile laps where runners eat a whoopie every lap, with solo mile, relay team, and endurance divisions on the College of the Atlantic campus.
Back Cove Backyard Ultra in Portland, ME on July 10, 2027 has runners complete a roughly 4.16 mile loop each hour until only one runner remains, with staffed aid and free parking.
A 9 mile two lap trail race on Bradbury Mountain with hilly technical single track, capped at 140 runners and organized by nonprofit Trail Monster Running.
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 race on Blue Hill Mountain, Maine, featuring looped 5k, 10k, 25k and 50k courses across wildflower fields, technical forest trails, and coastal viewpoints.