Trail Running calendar near Weston 2026-2027

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.

An inclusive multisport festival at Pawtuckaway State Park on 09/26/2026 offering a 0.4 mile swim, 5.5 mile trail bike and 3 mile run in single sport, two sport, relay or full triathlon formats. No chip timing; safety gear is required.

A trail based 5K obstacle course race at Wasserman Park on September 26, 2026, featuring 12 or more beginner to intermediate obstacles. Entry is limited to 200 participants and the fee is $40.

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 at the Assabet River National Wildlife Refuge in Sudbury MA include a 10K, a 30K and a 6 hour timed event. The course uses dirt and gravel double track trails with two aid stations and cupless fueling.

A community run at Shedd Park in Lowell offering a 5K, a 10K trail run, and a kids 1 mile fun run. Proceeds support the Lowell Parks and Conservation Trust and its conservation and education programs.

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.

A timed trail ultra in Cumberland RI offering 8 hour, 12 hour, and 34 hour options for individuals and teams up to four. The 4.2 mile loop mixes smooth trail and moderately technical rocky sections.

Trail races in Groton, Massachusetts on October 4, 2026, organized by local running and trails groups. Two distances, 9.5 miles and 3.4 miles, total entries limited to 250, online registration closes October 3.

A 26.4 mile trail marathon on Connecticut’s Nipmuck Trail featuring rocks, roots, mud and wood bridges, with an optional two-person relay and elapsed time cutoffs. Organized by the Shenipsit Striders in Ashford, CT.

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.

A 5K trail race and 1-mile fun run at Tibbetts Field in Madbury, NH on October 4, 2026, featuring a 2-mile loop through Powder Major Forest over natural terrain. A portion of proceeds will support a local family in need.

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.

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 community 5K and 1 mile fun run on October 11, 2026 supporting Unified programs at Beckwith and Dighton Middle Schools. Fees vary by registration period and registered runners receive T-shirts and awards for top finishers.