Trail Running calendar near Portland 2026-2027

A 21k trail race on Pleasant Mountain in Bridgton, Maine on Sep 27, 2026. The course features technical single track, steep climbs, one aid station, mandatory mountain safety gear, and post race food, beer and live music.

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 last person standing trail ultra on a 3.5 mile forest loop in Center Conway, NH, open to all ages and abilities. The event includes a minimal midway aid station, camping option Friday, food on Saturday, awards and participant swag.

A 25K trail race at Edwin L. Smith Preserve in Kennebunkport, Maine, benefiting the Kennebunkport Conservation Trust with registration capped at 100.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

A trail 5K in Oxford, Maine starting and ending at Oxbow Beer Garden to benefit Mission Working Dogs, with limited race shirts and a beer ticket for attendees 21 and over.

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 rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

A human powered 100k in Norway, ME combining 25k running and 75k cycling across six trail systems. Solo and duo formats, cupless aid stations, and proceeds supporting local youth and land trust programs.

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.

Mountain up-and-down race at Cranmore Mountain in North Conway offering 10 km and 5 km options, USATF sanctioned and $7,500 in prize money for 2026.

A trail event at East Windham Conservation Area offering a five loop 50k and a single loop 10k with two aid stations per loop and volunteer support. Finishers receive a cotton event t shirt.

A 4.1 miles trail race in Ravenswood Park, Gloucester, held October 18, 2026, as part of the North Shore Trail Series. The course uses single-track and carriage roads, with online registration closing October 15 and race-day registration av..

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

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 5K trail run on October 31 2026 at Wells Reserve at Laudholm. Timed course with water stations and awards, with proceeds supporting coastal conservation and restoration.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.

Night-time trail races of 5k and 10k at Cranmore Resort on November 7, 2026, requiring headlamps and featuring reflective course markers and LED lighting.

A community 5K walk and run with a kids fun run at Windham Woods School on November 14, 2026 in Windham, NH.