Trail Running calendar near Great Barrington 2026-2027

A women only 5K obstacle mud run in Albany, NY on July 12, 2026 featuring more than 18 obstacles. The event welcomes participants aged seven and up and is presented as non competitive with an emphasis on fun and teamwork.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

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..

Part of the Shawangunk Runners summer series since 1974, the Blueberry Run in Kerhonkson features a 4.1 mile loop around Lake Minnewaska plus shorter kids races, with parking at Minnewaska State Park and no registration fee.

A trail race at Soapstone Mountain in Somers, CT featuring a 5.5 mile loop with six ascents, a cupless water stop, a 50 runner cap, and course sections that can be steep and rocky; organized by the Shenipsit Striders.

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.

An eight hour track event at Clapp Park in Pittsfield with a virtual option, chip timing, on course bottle drop aid, and age division awards. Proceeds support the AYJ Fund and several discount codes are available.

Tappen Brook 5K on August 9, 2026 in Bridgewater, CT is a 3rd annual trail race on the new Bridgewater Town Park trails, featuring packed-dirt paths, gentle hills and views of Lake Lillinonah. The event is organized by local land trust and..

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 community eight hour loop run at Crandall's Pavilion in Tolland, CT, organized by the Shenipsit Striders. The free event features repeated roughly 5K trail loops, potluck food, and an optional donation jar.

Trail races at Fahnestock State Park near Cold Spring, NY on Aug 15, 2026. Distances include 50K, 25K, and a 5.5-mile option on mixed dirt roads and technical single track with on-course aid and a post-race meal.

Experience a rolling cross country run through the forests and meadows of the Landis Arboretum. This sanctioned 5K race offers views of the Schoharie Valley and access to scenic trails and gardens.