Trail Running calendar near Springfield 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 women only 5K obstacle mud run at Carter & Stevens Farm in Barre, MA on September 20, 2026. The course has 18+ obstacles, welcomes participants ages seven and up, and emphasizes teamwork over competition.

A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.

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 trail-based 5K obstacle course at Wasserman Park on September 26, 2026, featuring 12+ beginner to intermediate obstacles. Entry is limited to 200 participants, costs $40, and early registrants receive a race shirt and finisher medal.

A trail event on the Moosup Valley State Park Trail featuring 5K, 8K, 10K and a Kids Fun Run. Parking and the finish are at Weidele's Pizza with post-race food, awards and a medallion or shirt option.

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 1 mile kids loop, with trails, on-course support, family activities, and proceeds benefiting local conservation and education programs.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

A 15-mile trail event at Mohawk Mountain Ski Area in Cornwall, CT with 7,140 feet of elevation and a 12-hour limit; participants may run, hike, walk, or compete in a relay, with registration listed as free for the stated window.

A 30 Hour looped trail event at Roosevelt Forest in Stratford CT on October 3 and 4, 2026 offering distances from 26.2 miles to 100 miles on a 2.5 mile loop with central aid at the pavilion and a finisher buckle for 100 miles.

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 timed endurance running event in Cohoes, NY on October 3, 2026 offering 6 hour, 3 hour and 1 hour options plus relays. It benefits Flutters of Hope, a nonprofit supporting people and families affected by eating disorders.

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.

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

A 26.4 mile trail marathon on the Nipmuck Trail in Ashford CT with varied terrain and wood bridges. Organizer Shenipsit Striders also offers a two person relay that splits the course into two halves.

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.