Trail Running calendar near Chester 2026-2027

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

A six hour weighted trail race in Mansfield, MA on October 17, 2026 where runners complete as many 2.5 mile out-and-back laps as they can, scoring pound-miles called Kz by multiplying lap distance by the weight carried.

United We Move Trailfest on October 17, 2026 at Fall River Bioreserve offers walk, run, and ride routes of varying lengths to support the Annual Campaign; routes are marked and GPX files are available.

An off-road *50K* through interconnected woodland preserves in Guilford, Connecticut, featuring rocky single track and rolling forest roads. The course is set for experienced trail runners and has limited entries.

A fall trail event at Grills Preserve in Westerly with 10 mile and 10 km courses across single-track trails and riverfront sections. Club timing is used, orange clothing is required, and post-race refreshments are provided.

A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.

A fall trail race at Mt. Tom State Park on October 24, 2026, with single and relay options from 5k to 25k on rugged single-track terrain. The event supports Kestrel Land Trust and includes aid stations, medical crews, and awards.

A community run at Ives Farm hosted by Cheshire Community YMCA and Cheshire Land Trust. Features a trail 5K, a youth Y Cup relay with elementary teams, a free Pumpkin Dash for young children and family fall activities.

A backyard ultramarathon and festival at Waters Farm in Sutton MA where runners complete a 4.167 mile loop each hour on the bell until one remains. The weekend features live music, hay rides, a kids fun run, farm tours, and local food.

A trail event at Muscoot Farm on October 25, 2026: a five-mile race plus two kids races, kids medals, and Farm Bucks for finishers.

A fall trail 5k in Berkley MA combining running, rucking, and walking to honor military, first responders, and K9s. Dogs are allowed on leash with a waiver and proceeds support local canine and service organizations.

A 5K Run / Walk and Kids Fun Run at Hallock State Park on October 25, 2026, with a virtual 5K option. Proceeds support the Long Island Greenway and include a post-race wine crawl with vendor specials for participants 21 and over.

A stadium stair-climb at Gillette Stadium where participants run, walk, or roll through about 5,184 steps in support of Homes For Our Troops. The event offers team and wheelchair waves, optional fundraising, and spectator registration.

Trail half marathon, 5K and a kids fun run in Garrison, NY on October 25, 2026, benefiting the Friends of Philipstown Recreation. The courses run through Hudson Highlands State Park and pass Osborn Castle on private property reserved for re..

A trail running event at Red Wing Recreation Area near Lagrangeville, NY, offering 100k, 50k and 10k looped courses with on-course aid, finisher medals and awards for top male and female finishers.

Timed trail event at Gurski Farm in Brookfield CT featuring an 8 hour race, a 4 hour option, and a 5K canicross on a 4 mile loop.

A 10K trail race in Penwood State Park featuring technical single track on the Metacomet Trail and rocky runnable terrain. No aid stations so runners must carry hydration for 6.2 miles; proceeds partly support NAMI.

Experience a single loop marathon or half marathon on historic carriage roads in the Rockefeller State Preserve. Enjoy views of the Hudson River and stone bridges on a course with no pavement or cars.

A looped 3.1-mile trail course at White Barn Farm in Wrentham MA with distances from 5K to 50K and a central aid station. Runners complete repeatable laps and may stop after any finished loop.