Trail Running calendar near Portland 2026-2027

Test your endurance at Pineland Farms in Maine with this backyard ultra trail race. Run a 4.2 mile loop through pristine wooded trails and see how many laps you can complete in this last person standing format.

Experience a flat and non technical trail race at Cherry Hill Farm in Gorham Maine. Choose between 50k 25k or 10k distances consisting of multiple loops around the scenic farm property.

A trail running weekend around Mirror Lake in West Newfield, Maine, with laps of about 3.6 to 3.8 miles through forest roads and singletrack. The weekend includes a Saturday gravel ride, onsite camping, youth runs, and a post ride gathering..

Three trail races in Camden Hills State Park present 10K, 20K and 50K courses around Mount Megunticook, with routes ranging from steep singletrack to wide gravel trail and an Indigenous land acknowledgement and giving option.

Trail races at Bear Brook State Park near Allenstown, NH offer a GPX navigated half marathon and a variable ultramarathon between 50k and 100k, with minimal course markings and cup free aid stations.

Thunder Run is a 5K trail race with more than 20 obstacles through woods and hills in Candia, New Hampshire on September 12, 2026. Organized by Raymond Area Rotary, 100% of proceeds support local and selected international projects.

A September mountain race at Echo Lake State Park offering a five mile course and a half marathon that climbs over 4,300 feet of vertical. Courses run on granite ledges and exposed ridges with remote aid stations.

Big Brad Ultras at Bradbury Mountain State Park offers 25K and 50K options on a 15.5 mile single track loop. The course features technical terrain, multiple aid stations, drop bag access, and significant elevation gain.

The 12th Annual Skyline Farm 5K Trail Run & Walk on September 13, 2026 offers a scenic course through fields, hills and woods, a free Kids' 1K with prizes, post-event food and music, and awards including gift certificates and pies.

An annual community trail event at Mount Agamenticus offering timed **1 Mile** and **5K** courses from the summit, with proceeds supporting conservation and education and a raffle for participants.

Experience a scenic run through wooded conservation trails finishing at the Hooksett Public Library. This community event features a 5K trail race and a half mile kids fun run to support local youth programs.

A 5K trail race at Loon Mountain on September 20, 2026, as part of the 51st NH Highland Games, with 800 ft of elevation gain across dirt trails, service roads and ski trails. Registration includes a race shirt and festival admission.

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.

A traditional up and down mountain race in Waterville Valley, NH on September 20, 2026 covering about 7 miles with 3000 feet of ascent; youth entry is available and day of registration is offered.

A community trail festival in Arundel, Maine offering 5k, 10k and half marathon distances on the ACT and Eastern Trail, with participant shirts and medals, a free kids' bike race, live music, and food.

An inclusive multisport festival at Pawtuckaway State Park on 09/26/2026 offering a 0.4 mile swim, 5.5 mile trail bike and 3 mile run in single sport, two sport, relay or full triathlon formats. No chip timing; safety gear is required.

A looped trail ultra at Wolfe's Neck Farm in Freeport, ME, on a just over 5 mile dirt loop with stairs, bridges, and about 570 feet of gain per loop. Distances include 50 mile, 30 mile, and 10 mile options.

A 21k trail race on Pleasant Mountain in Bridgton, Maine on September 27, 2026. The route includes steep climbs, technical single track, one aid station, and a postrace gathering with food, beer for 21 plus, and live music.

An ultramarathon in Center Conway NH using the Last Person Standing format on a 3.5 mile loop of forest singletrack, trails, fields, and logging roads with about 250 feet of gain per lap. Camping is available the night before.

A 25 kilometer trail race at the Edwin L. Smith Preserve in Kennebunkport on October 3, 2026, with proceeds supporting the Kennebunkport Conservation Trust. Registration is capped at 100 and a shirt-included cutoff is on September 5.