Maine
Maine Trail Running Calendar 2026-2027
Explore the best trail runs in Maine for 2026-2027! Our updated list features 33 exciting trail runs across the region. Find your next trail run in Maine below and join the trail community at these great events!
September 2026
Experience an all trail ultra marathon through the woods and coastal farmlands of Freeport Maine featuring 50 mile 30 mile and 10 mile distances on a scenic 5 mile loop.
A 21k mountain race in Bridgton featuring technical single track trails and significant elevation gain across the iconic ridge of Pleasant Mountain.
A Downeast Maine trail event offering an eight mile point to point, a two person relay and a 5k finishing at Middle River Park with post race food and awards.
A 5K held at Bowdoin College on September 27 2026 featuring a two-lap grass and dirt trail course around the Pickard Field complex with a $20 entry fee.
October 2026
A 5k trail run and 1 mile trail walk at the Northeast Equine Sanctuary on October 3, 2026, raising funds for the sanctuary with yoga, a vegan BBQ, raffle and family activities.
A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust.
A 5k trail run and walk in Oxford, Maine, starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs, offered in-person and virtually.
The 26th North American Wife Carrying Championship returns to Sunday River in Newry, Maine on October 10, 2026. Teams of one man and one woman race a 278 yards obstacle course with log hurdles, a sand trap, and the Widow Maker water hazard.
Trail races in Sullivan, Maine on October 10, 2026 across Baker Hill and Long Ledges with distances 52K, 17K, 12K and 6K; cupless race and limited on-course support.
A 3.1 mile obstacle and fitness course in Wiscasset with at least ten moderate obstacles over uneven terrain, water and mud; pre registration available, fee $45.
A fully human powered 100k in Norway, Maine combining 25 km of trail running and 75 km of cycling across six preserves, with proceeds supporting local nonprofits.
A coastal 5K at Hermit Island Campground supporting Marine Mammals of Maine, with timed and untimed in-person runs, a weeklong virtual 5K, a kids 1-mile fun run, raffle, and prizes for top human and canine finishers.
A mountain run from the SuperQuad base to Sugarloaf's 4,237 foot summit, gaining nearly 2,500 feet over about 2.5 miles with postrace lunch and awards.
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.
Trail events in Orland, Maine: a 6.2 mile climb to Great Pond Mountain's 1,009 foot summit and a 1 mile fun run to the Dead River banks.
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.