Trail Running calendar near Westfield 2026-2027

Experience a four part summer trail series at the Dublin School Outdoor Center. Run a scenic 5K loop featuring singletrack and rolling terrain while supporting local charities and community needs.

A memorial 5K run and walk at Owen Bell Park in Dayville CT that raises funds for a scholarship for Killingly Ag-Ed seniors. The day includes a 5K, a walk, and a kids fun run on off-road paths with possible trip hazards.

A 1 mile out and back on the Farmington Canal Heritage Trail with a crushed gravel surface and hand timing. Held July 19, 2026 in East Granby in two waves with limited parking; proceeds benefit charities.

Two trail-focused races at Beartown State Forest in Great Barrington, MA: a 5-mile loop around Benedict Pond and a roughly 13.5-mile half with significant climbing and technical terrain. The event is cupless with limited parking and shuttle..

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 30 km singletrack mountain race in the Catskills on July 26, 2026 with about 4,800 ft of climb and a six hour cut off. The remote route has limited aid, wave starts, and entry requires qualifying standards.

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 trail running event at Ward Pound Ridge Reservation offering 25K, 50K and 50M courses across wooded singletrack and carriage roads with runnable sections, ridge views, aid stations, and GPX course files.

Muddy Dash Boston is a family-friendly 5K mud run at 508 INTL Adventure Sports Center on August 1, 2026, with obstacles, mud pits and slides, plus a pre-party and an after-party with music and food.

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 trail event at Noon Hill Reservation in Medfield offering a 10 mile loop plus 50K and 40 mile ultra options, mostly singletrack with roots, rocks, and a scenic Noon Hill vista; proceeds benefit The Trustees of Reservations.

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 race from the base of Stratton Mountain to the top with 2 km and 5 km options. Proceeds support the SMST2 professional cross country ski team and include a post race meeting with US Ski Team athletes.

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

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.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K, and 5.5‑mile options with aid stations, a post-race meal, and proceeds supporting park conservation.