Trail Running calendar near Keene 2026-2027

A 26.4 mile trail marathon in Ashford, CT on October 4, 2026 with rugged terrain and a two-person relay option.

Keene Family YMCA Fall Foliage Trail Races feature 5K and 10K trail courses starting and finishing at the Keene YMCA, with chip timing, age-group prizes, and proceeds supporting YMCA programs and access.

Join the annual Run Stanley event at Stanley Park for a variety of trail races including a 5K K9 run and an accessible 1 mile stroll. Support local wildlife sanctuary maintenance while enjoying a community day in the park.

Trail running at Tibbetts Field in Madbury includes a 5K and a 1 mile fun run over natural terrain through Powder Major Forest, with proceeds supporting youth recreation scholarships.

Trail races at Houghton's Pond in the DCR Blue Hills Reservation follow rolling dirt roads and forest paths with rocks and roots. Two distances are offered, about 7 miles and 3.7 miles, with notable elevation change on each course.

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

Trail event in Bradford Vermont with looped mountain course, 30 hour, 12 hour and 6 mile options, tarot themed awards and a 100 runner cap.

A community run on October 10, 2026, organized by the Lebanon Recreation, Arts, and Parks Department, following the Rail Trail from Enfield along Mascoma Lake and the Mascoma River to a finish in Lebanon. Fees change before race week and pa..

Community 5K and a 0.5 mile youth run at Pitney Meadows Community Farm on October 10, 2026. The mixed surface, spectator friendly course runs on grass and stone dust and raises funds for the farm's programs.

On October 11, 2026 the HFC Striders Cross Country Festival returns to Wayland for its 20th running, featuring 3K youth races across age groups and two 5K open races, with awards and proceeds benefiting Wayland High School.

A rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

A time-based event in New Salem MA offering 12 hour and 24 hour run or walk options around the town common on October 11, 2026.

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.

Trail event in Brookline, NH with multiple races on the Granite Town Rail Trail and proceeds supporting local conservation.

Timed endurance running at Champs Campground in Whitehall NY on October 17 and 18, 2026. Choose a 6 hour, 12 hour, or 24 hour race on a flat 0.30 mile loop with aid station, camping, and limited fields.

Explore the scenic trails of 100 Acre Woods in Malta, New York. This community event on October 18, 2026 features 2k, 3k, and 5k trail runs. All proceeds support local trail maintenance.

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 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

Backyard ultramarathon at Waters Farm with a 4.167 mile hourly loop, a 4.2 mile community run, a free kids fun run, and a full festival.