Trail Running calendar near Pownal 2025-2026

Celebrate the season with the Jackson 5k Turkey Trot and kids 1k on scenic trails in Jackson, New Hampshire. This family friendly event brings the community together while raising funds for Jackson Grammar School and Girls on the Run.

The TruStrength "Uphill Will" 24 Hr skimo will take place in Greenwood on Saturday 14 March 2026.

Riverlands 100 & Relay is a trail ultramarathon held in Turner, Maine, on May 2–3, 2026. The event centers on a 100‑mile race with a relay option, inviting solo runners and teams to tackle the course over two days. The race information page..

Run laps on a scenic 2 mile single track loop around White Lake in Tamworth, NH with 6, 12 or 24 hour timed options and a beach start and aid station. Costumes encouraged and bring your own hydration.

Take on the classic Chocorua Mountain Race, a rugged 23 km trail run through White Mountain terrain with steep climbs and rocky technical summit trails. Expect big elevation gain, self supported aid rules, and sweeping summit views.

Explore scenic trails south of Sebago Lake at the inaugural Otter Pond Trail Races in Standish, Maine on June 13, 2026. Choose a timed endurance Dawn to Dusk challenge, a 10K or a kids run while supporting Bonny Eagle Athletics.

Race The Cog invites runners to tackle the Mount Washington summit via the historic Cog Railway tracks on June 20, 2026, with 2.75 or 5.5 mile options. Expect steep, rocky terrain and a summit Cog train return for the shorter course.

Test your limits at the Back Cove Backyard Ultra in Portland, ME, where runners complete a 4.16 mile loop every hour around Back Cove Park until one remains. Enjoy a flat scenic course, basic aid stations, and a friendly volunteer crew.

Take on Loon Mountain's Upper Walking Boss on July 12 in Lincoln, New Hampshire, a roughly one kilometer black diamond climb that will test every runner. Men, women and U20 categories plus a $1,500 challenge purse raise the stakes.

Tackle the Baldface Scramble in New Hampshire's White Mountains with a rugged 29K or a shorter 14K loop over the Baldfaces. Expect steep ledges, exposed scrambling and technical single track for a true mountain challenge.

Tackle rugged, high climbing trail ultras in the White Mountain National Forest with 20, 50 and 100 mile options. Expect technical trails, huge elevation, cupless aid and camping options for an epic mountain challenge.

Firebird Trail Races in Windham Falmouth Maine feature 50K, marathon and 13M races on technical single track through Lowell Preserve. Tackle rocky, root strewn trails with friendly aid stations and earn a carved wood Firebird medal.

Explore Waterville Valley trails at the Black Bear Trail Races on August 29. Choose from a family friendly 1 mile fun run up to a challenging 50K around nearby 4,000 foot peaks, with finishers awards, post race snacks and a finish festival.

Test your limits at the Last Man Standing Ultramarathon on September 5, 2026 at Pineland Farms in New Gloucester, Maine. Run repeating 4.2 mile wooded loops until a single finisher remains in this backyard ultra classic.

Run the Megunticook Trail Festival in Camden Hills State Park on Sep 12, 2026, with 50K, 20K and 10K options across rocky summits, ocean views and classic Maine woodland trails. Entries are limited so register early.

Enjoy scenic 1 Mile and 5K trail runs and hikes at the Annual Trail Challenge on Mount Agamenticus in York, Maine Saturday September 19. Proceeds support conservation and education and a community raffle makes the day festive.