Trail Running calendar near Holyoke 2026-2027

A 5.5 mile mountain trail race at Soapstone Mountain in Somers CT organized by Shenipsit Striders. The course features six ascents, steep rocky sections, a field capped at 50 runners, and required online registration.

A 3.1 mile lap race at Chris Lewit Tennis Academy near Manchester, Vermont, held on wooded trails beside the West River. Net proceeds support veterans charities and all racers receive a free T shirt; family activities include river swimming..

A community 5K trail race at Legacy Park with professional timing, a post-run gathering featuring grilled burgers and local beer and wine tasting for registrants 21 and over, and a limit of 500 participants.

A family-friendly 5K mud run on August 1, 2026 at 508 INTL- Adventure Sports Center with obstacles, mud pits, a pre-party, and a post-race festival.

A 7-mile USATF sanctioned trail race in Barkhamsted, CT on 08/01/2026. Registration runs 05/03/2026 to 07/31/2026 with a $20 fee and no race day registration; results posted online by Greystone Electronics.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

A community fundraising day in Groton, MA on August 5, 2026 featuring an 8.4 mile three-person relay, kids single-loop race and Little Lambs mini runs, followed by barbecue and activities, with proceeds to six local charities.

A seaside set of timed ultra-marathon events at Colt State Park in Bristol, Rhode Island, offering 6 hour, 12 hour, and 24 hour formats with separate entry periods and fees.

Trail Animals Running Club holds 10M, 50K and 40M trail races on a mostly forested 10-mile loop at Noon Hill Reservation in Medfield MA.

Lover's Lane in Chester, VT is a timed 6 or 12 hour loop event on August 8, 2026 featuring a 1.8 mile loop with 280 feet of elevation per loop. The fat ass style event provides basic aid and supports local recreation and recovery organizati..

A forested 5K through newly developed trails at Bridgewater Town Park in Connecticut, hosted by the Bridgewater Land Trust and the Bridgewater Recreation Commission. Participants receive a race-day gift and top finishers earn awards.

A summit trail race on Stratton Mountain with youth and open distances, prizes, raffle awards, and proceeds supporting the SMST2 professional ski team.

A multi day timed trail event on a Winchendon farm using a roughly two mile loop. Runners choose from six hour day or night, 12 hour, 24 hour, or 48 hour formats under the Sturgeon Moon.

A free eight hour trail event in Tolland on August 15, 2026 where runners complete as many 3 mile loops as they wish. The event includes on-site food, a potluck, and a GPX course map.

A 5K off-road trail run, walk, and hike at White Barn Farm through Wrentham conservation land. The event is part of the Farm to Trail 5K Series and raises funds to support local agriculture and food pantry donations.

Experience a community trail run through Elm Ridge Park benefiting the Rocky Hill Fire Department and Library. This event features a two loop trail course for adults and a fun medal race for kids.

A chip-timed 5K run/walk at Brimfield Winery on a two-lap grass course with hills, race swag, a wine pour, and age group awards; a one-lap 1.5 mile division is available.

An eight mile trail run on a well-groomed unpaved carriage path beside the Ashokan Reservoir in West Hurley, NY, limited to 100 runners with age-group awards and a commemorative item for early registrants.

A six-hour loop ultra at Jug End State Reservation in Egremont, MA featuring a 4.2 mile course through woods, fields and an apple orchard. Age-group awards and a handmade finisher mug; proceeds benefit Louison House.

A trail running festival at Thacher State Park on August 23, 2026, offering **10K**, **13.1M**, **26.2M** and **50K** courses that share the same first 10K loop. The cupless event has multiple aid stations, post-race food, and medals for ma..