Trail Running calendar near Springfield 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.

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.

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 lap race on Mansfield's WWII Veterans Memorial Trail. Competitors carry measured weight each lap and score pound-miles called Kz, with the highest total in each division winning.

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.

Bimblers Bluff 50K on October 18, 2026 in Guilford, CT is an off road ultramarathon over rolling forest roads and rocky single track through interconnected woodland preserves. The course does not require multiple loops and includes aid stat..

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 trail event at Ives Farm featuring a 5K trail race, a youth team relay, and a free kids Pumpkin Dash, plus family activities and proceeds supporting local YMCA and land trust projects.

A mountain trail race in Keene NH on October 25, 2026 covering 4.9 miles with 1,650 feet of elevation across four laps; the event benefits the Keene Community Kitchen and offers prize money, age-group awards, and raffles.

A fall trail race at Powisset Farm in Dover on October 25 2026 offering four distances, one water aid station, post race cider donuts and family activities with awards for top finishers.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

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 stair climb at Gillette Stadium where participants walk, jog or climb around the lower bowl while music and team highlights play. Net proceeds support Homes for Our Troops.

Trail races at Red Wing Recreation Area in Lagrangeville, NY, featuring 100k, 50k and 10k looped courses with notable elevation. The 50k and 100k are UTMB Index races and all finishers receive custom medals.

Experience a unique timed trail event at Gurski Farm featuring a four mile loop of rolling farm trails and single track. Choose between eight hour, four hour, or 5K options in a community focused environment.

A Stadion 5K obstacle race at Fenway Park on November 7-8, 2026, featuring 20 obstacles and a finish across home plate. The weekend also includes a 1 to 1.5 km kids race, spectator tickets, team options, and a service member discount.

A multi hour loop event on the New Boston Rail Trail near the fairgrounds offering 6, 12, 24 and 30 hour individual and relay options, chip timing, a central aid station, team entries, pacer rules and 100-mile buckles.

A backyard ultra at Kenty's Farm on November 7, 2026 where runners complete repeated 4.1666 mile laps until one remains; also offers 6, 12 and 24 hour timed options and a single-lap competition.