Trail Running calendar near Great Barrington 2026-2027

A 5.5 mile trail race at Soapstone Mountain with six ascents and about 1500 feet of climb. The field is capped at 50 runners for parking reasons and online registration is required.

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 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.

A 5K mud run on August 1, 2026 at 508 INTL- Adventure Sports Center in Boston, featuring obstacles, mud pits and slides, plus Pre-Party and After-Party with music, food and beer. Kids are welcome and light quick-dry gear is recommended.

An eight hour track endurance event at Clapp Park in Pittsfield, MA featuring a certified 0.355 mile loop, chip timing with live leaderboard, on-course bottle drop and age group awards. Proceeds support the AYJ Fund.

A forested 5K on the new trails at Bridgewater Town Park in Bridgewater, CT. The 3rd annual event features mixed natural terrain, views of Lake Lillinonah, participant gifts and awards for top finishers.

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 community running event in Tolland, CT featuring a marked 5K trail loop run repeatedly over an eight hour period, potluck food and grill items, raffle tickets awarded per loop, and a 50th anniversary gift for runners who complete at least..

Trail races in Fahnestock State Park near Cold Spring, NY, offering 50K, 25K and a 5.5-mile course on varied terrain with on-course support, post-race meal, and proceeds supporting land conservation.

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.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

A mountain trail event at Belleayre Resort on August 16, 2026 with a demanding 25K and an 8K on ski slopes. The event runs as zero carbon and raises funds for The Catskill Center.

A 6 hour timed ultra and a 4.2 mile memorial run at Jug End State Reservation in Egremont MA on August 22, 2026. The loop covers woods and orchards with 830 feet elevation per lap and benefits Louison House and Dana Farber.

A 4 mile open time trial on the single track trails of Schenectady Central Park with individually timed laps. All proceeds go to Hive of Hope, a community organization supporting recovery through connection and movement.

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..

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

An inclusive trail festival at Northfield Mountain on August 29, 2026 that centers queer and trans runners and allies. It offers a 20k prediction race, an untimed 5k fun run or hike, and a Kid's Run with community-focused prizes.

Timed loop trails on Wachusett Mountain with 7, 14, 21, and 28 mile options over ski slopes and single-track. Participants have 10 hours to finish, with weighted vest options and marked courses; finishers receive a shirt and patch.

Sterling Down & Dirty 5K is an annual family friendly obstacle race on Stratford Short Beach each September. Participants tackle more than 18 obstacles, join teams to fundraise for the Sterling Community Center, or volunteer on race day.

A multi-division trail event on the Shawangunk Ridge near Rosendale NY offering 70 mile, 30 mile and half marathon options on an unsupported, fully blazed route with shuttle access and finisher shirts and medals.