Trail Running calendar near West Bayside 2026-2027

A six-race trail series across Oxford Hills preserves from May to October, with each course about 3.1 Miles. Season preregistration is $72, single races $15, and student races are $5 each.

Experience Maine's premier trail running festival featuring races from 5K to 100K. This multi day event includes a 30 hour endurance challenge, dog friendly canicross races, and a sunset run at Pineland Farms.

A 5K trail event on May 30, 2026 at Danvers YMCA Camp in Boxford with separate courses for runners and for walkers and waggers, pond and vernal pool scenery, prizes, post-race treats, and registration benefits.

Run of The Fellowship is an in-person trail event at Clifford Park in Biddeford, Maine on May 30, 2026. It offers a 5K route and a longer full quest option, welcomes costumes, and is pending final permits and insurance.

A 23K mountain trail race in Tamworth NH with roughly 4,800 feet of climbing, a technical loop over the 3,478 foot summit of Mount Chocorua, mandatory mountain safety gear, and inclusion in the White Mountain Endurance Cup.

A six mile trail race at Bradbury Mountain in Pownal, Maine that begins the Bradbury Mountain Trail Race Series. The course follows single and double track trails with rolling hills and a race cutoff of 1 hour 48 minutes.

A ninth annual trail race through Dogtown Common on a rugged 5.4 mile course that mixes carriage roads and technical rock sections. Walkers are welcome, course maps are available, and prizes and event shirts are offered.

A community fun run on 06/13/2026 behind Madbury Town Hall with a 1K kids run and a 5K route through Kingman Farm trails. Registration is free and donations for park improvements are accepted on the day.

A mountain trail race from the Mount Washington Cog Railway base to the summit in Bretton Woods, NH, with a 2.75-mile summit option (train descent) or a 5.5-mile roundtrip.

A six hour timed endurance event on a flat 4 mile rail-trail loop in Poland, Maine; participants may run multiple loops with total mileage recorded and recognized, and paid entries include an event shirt.

A timed 5K loop through woods and fields at the Maine Outdoor Wellness Center on June 20, 2026. Bibs, water, snacks, and family activities are provided and a $15 registration supports community building and programming.

Muddy Princess Boston is a women only 5K obstacle mud run at Kimball Farm in Haverhill on June 21, 2026. The course has 18 plus obstacles and is open to women aged 7 and up who may run, jog or walk.

Field & Forest 5 Miler is a roughly 5 mile trail race on the Crystal Spring property in Brunswick, ME. The mostly off pavement course has single track and wood bridges, and the field is limited to 50 runners.

A trail 5 km race at Libby Hill Forest Trails in Gray, ME on June 21, 2026. Online registration is $15 through June 19, race day registration is $20 and students enter free. Proceeds support trail maintenance and door prize drawings are pla..

A small weeknight trail race series around Portland Maine from June 25 to July 30 2026, featuring races of about 5K to 6.5 miles, capped fields, partnerships with local land trusts, and series prizes for those who complete three races.

Ultratrax Cranmore in North Conway, NH is a single day endurance walk on June 27, 2026 offering 7, 14, 21 and 28 mile loops with a 10 hour cutoff. The course follows forest singletrack and old ski trails with aid stations and timed results.

A charity team challenge on June 27, 2026 in Bristol, NH that recreates Special Forces mission tasks. Teams of 6–12 choose Operator or Recruit levels, with awards for top teams, MVPs, fundraising leaders, and participant milestones.

A community trail festival in East Bayside, Portland on June 28, 2026 featuring a 10K run, 15 or 30 mile bike rides, and a 2 Miler. Registration proceeds support Portland Trails and the Bicycle Coalition of Maine.

A 5K obstacle mud run in Minot, Maine on June 28, 2026 for women and girls aged 7 and older. The course includes 18 plus obstacles and emphasizes a non competitive, teamwork oriented experience.

A family oriented 5k fun run in Tamworth, New Hampshire centered on historic Ordination Rock during July 4 celebrations. Organized by the Tamworth Outing Club, registration includes a bandana, ice cream, and a bib raffle entry.