Trail Running calendar near Milton 2026-2027

A 5K trail run and a 1/4 mile kids fun run at Felix Neck Wildlife Sanctuary in Edgartown, MA, with scenic trails and birdlife. Proceeds benefit the sanctuary's wildlife protection, education, and conservation programs.

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.

A Keene State College alumni cross-country meet on 09/12/2026 at the Keene State Athletic Complex featuring a men's 5K and a women's 2 Mile race; registration runs 09/06 to 09/12 with a $25 fee per event.

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 free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

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 community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

A community 5K in Jaffrey, New Hampshire on September 19, 2026, offering two course options: a mixed woods trail and a straight rail trail. Proceeds benefit the Jaffrey Firefighters Company Inc.

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 community 5K in Hillsborough, NH on September 20, 2026, organized by the Hillsboro Fire Department. The off-road course may be uneven and strollers are not recommended; registration runs March 25 to September 19 with a $30 fee.

The Arc'teryx Run Boston will take place in Milton on Sunday 20 September 2026. You can run 10 kilometers.

A 5K trail run at Goddard Park in Warwick, RI on September 26, 2026, with a bayside course and start and finish near the golf course clubhouse. Open to all ages, with published entry fee tiers and on site parking and facilities.

A multisport festival for people who identify as women at Pawtuckaway State Park on September 26, 2026, offering triathlon, two sport, single sport and relay options on supported swim, trail bike and trail run courses.

An all-trail event on the Moosup Valley State Park Trail in Moosup, CT offering 5K, 8K, 10K and a free Kids Fun Run with post-race shirts or medallions and food at Weidele's; proceeds benefit a local Rotary charity.

Trail races and a six hour timed event take place on double track dirt and gravel trails at Assabet River National Wildlife Refuge in Sudbury MA. The race is cupless, aid stations are provided, and pacers are allowed for the six hour event.

A community run at Shedd Park featuring a 5K, a 10K trail run, and a 1-mile kids fun run, with educational displays and proceeds supporting LP&CT's conservation and education programs.

Survival of the F.I.T.test is a 30 hour trail ultra held in October as part of the F.I.T. Challenge calendar in Cumberland, Rhode Island. Results for past editions are published online after each race.

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

A 5K fall trail run and walk at Ryan Park in North Kingstown on October 3, 2026, benefiting the North Kingstown Firefighters Association. Registrations before September 14 include a race day t shirt and top finishers receive medals.