Trail Running calendar near Kennebunkport 2026-2027

Trail races of 5k, 10k and half marathon on the Arundel Community Trails with medals, shirts, live music and a kids bike race.

A multisport festival at Pawtuckaway State Park offering swim, bike and run options for people who identify as women. Choose an individual triathlon, two sport combo, single sport or a relay team in a non competitive setting.

Trail based 5K obstacle race at Wasserman Park on September 26, 2026 featuring 12 or more beginner and intermediate obstacles and limited to 200 participants.

Trail-based looped ultra at Wolfe's Neck Farm in Freeport featuring a new all-trail five mile loop repeated for ten, six, or two laps depending on distance.

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 10K, 5K run/walk and a kids 1 mile fun run at Shedd Park in Lowell supporting local conservation and education.

Last person standing trail ultra in Center Conway, NH on a 3.5 mile forest loop with camping, meals, swag and a beer mile the following day.

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.

An annual 5K cross country run or walk in Franklin Park supporting Boston Latin School Athletics. Team registration is new for 2026 and fees are tiered with free entry for BLS students.

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

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.

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 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 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 event in Brookline, NH with multiple races on the Granite Town Rail Trail and proceeds supporting local conservation.

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.

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.

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..