Trail Running Calendar Maine 2026-2027

A community 5K trail run and walk at Skyline Farm on Sunday, September 13, 2026, across fields, hills and woods. The day includes a free kids' 1K fun run, post-event food and music, and prizes for individual and team finishers.

Experience the summit of Mount Agamenticus with a 5K or 1 mile trail race. Support local conservation efforts while running or hiking through Maine trails and participate in a raffle for all entrants.

Pair up for a three hour endurance relay on a two mile loop of trails and fields. Alternate laps with your partner to accumulate the maximum distance possible in this team based challenge.

Trail races on maintained local trails in Arundel, ME offering 5k, 10k and half marathon options, plus a kid's bike race, participant medals and shirts, live music and food.

A looped trail event at Wolfe's Neck Farm in Freeport featuring roughly 5 mile loops on dirt trails with 50, 30 and 10 mile solo options plus relays, a single aid station at the start finish, and specific pacer and guide rules.

A half marathon across Pleasant Mountain's ridge on September 27, 2026 in Bridgton, ME. The course uses technical single track trails and includes tiered entry fees, a tech shirt, meal ticket and a finisher medal.

Trail runs in Whitneyville on 27 September 2026 with 8 mile and 2.5 mile courses through the Machias River Preserve, post race potluck, awards across age groups, and a raffle for a $100 gift certificate.

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 25 kilometer trail race through the Edwin L. Smith Preserve in Kennebunkport, Maine on October 3, 2026. Proceeds support the Kennebunkport Conservation Trust and registration is limited to 100 entrants.

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 human-powered 100K event near Norway, Maine combining roughly 25 km of trail running with 75 km of cycling between preserves. Proceeds support TruStrength Tomorrow and a portion goes to Western Foothill Land Trust.

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.

Little Duck 50k in Windham, ME on October 18, 2026 features 50k and 10k trail races at East Windham Conservation Area, run on a multi loop course with significant elevation and staffed aid stations.

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.

A fourth annual community run at Emmons Preserve in Kennebunkport offering timed 5K and 10K races plus a kids 1/2 mile fun run, music, family activities, a wood burned finisher medal and a raffle with local prizes.

A community 2.5-mile trail run at Thorne Head Preserve supporting local trails and education, featuring river views, a short technical section, no official timing, and a fall finisher's breakfast with a commemorative mug.

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.

Bold Coast Bash in Cutler Maine offers a coastal single track figure eight with a 50K ultra and a 10.5 mile fun run. The course features cliffs, rocks, mud, and bog bridging and requires mandatory safety gear and self support.