Maine
Maine Trail Running Calendar 2026-2027
Explore the best trail runs in Maine for 2026-2027! Our updated list features 38 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
A 21k trail race on Pleasant Mountain in Bridgton, ME, featuring steep ridge climbs, technical single-track, one aid station, and a finish-area afterparty with food and beer.
Trail running in Whitneyville, Maine on 27 September 2026 with an 8 mile race and a 2.5 mile run or walk through the Machias River Preserve. Courses feature singletrack and riverside sections plus post race awards and a potluck.
October 2026
Experience a scenic trail run or walk through the Northeast Equine Sanctuary in Maine. Enjoy yoga sessions and a vegan BBQ while supporting animal welfare among beautiful horses and autumn foliage.
A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, ME on October 3, 2026, with proceeds benefiting the Kennebunkport Conservation Trust and registration capped at 100.
Trail 5k in Oxford, Maine starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs; properly trained service dogs only and beer tickets for those 21 or older.
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.
A fully human powered 100K in Norway, Maine mixing 25k of trail running and 75k of cycling across six preserves, offered as solo and duo with charitable beneficiaries.
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.
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.
Trail running event in Windham, ME offering a 50k of five 6.5 mile loops and a single-loop 10k with aid stations and volunteer support.
Trail races in Orland, Maine with a 6.2 mile summit route over forested single track and granite slabs, plus a 1 mile fun run to the Dead River. The event supports the Great Pond Mountain Conservation Trust.
Holistic Hustle in Kennebunkport features a timed 5K, a trail 10K and a kids half mile fun run at Emmons Preserve on October 31, 2026. The community fundraiser includes music, family activities, finishers medals and a raffle.
A small community 2.5 mile trail run at Thorne Head Preserve on October 31, 2026, with river views, a fall breakfast, and proceeds supporting local trails.
A costumed, timed 5K trail run at Wells Reserve at Laudholm on October 31, 2026 that raises funds for coastal conservation and restoration.
November 2026
Trail ultra and 10.5 mile fun run on the Cutler Bold Coast. Figure eight single-track, self-supported with mandatory kit and a 10.5 hour course limit.
December 2026
A volunteer run, donation based marathon and half in Millinocket, Maine with USATF certified courses that may qualify for major marathons.
July 2027
A playful Bar Harbor event where runners eat a whoopie pie every 0.25 mile, competing solo, in relays, or in an endurance format.
Back Cove Backyard Ultra in Portland ME sends runners on repeated 4.16 mile loops around Back Cove Park each hour until only one runner remains.