Trail Running calendar near Copake 2026-2027

A forested 5K on August 9, 2026 at Bridgewater Town Park featuring new trails, modest hills, participation gifts, and prizes for top finishers.

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

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 free 8-hour trail event in Tolland, CT where runners complete as many 3-mile loops on a marked 5K-ish course as they like, with provided food and a potluck.

Trail races in Fahnestock State Park near Cold Spring NY offering 50K, 25K and 5.5 mile options 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.

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.

Mountain trail event at Belleayre Resort offering 25K and 8K courses, zero-carbon measures, and fundraising support for The Catskill Center.

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 timed six hour loop event on Aug 22, 2026 at Jug End State Reservation in Egremont MA with repeated 4.2 mile laps and a 0.75 mile final loop.

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.

Charity 5K run and 1.5 mile walk in Huntington MA on a mixed pavement, field and trail course that finishes at Littleville Dam.

An obstacle-based 5K at Short Beach, Stratford on September 12, 2026, with 18+ obstacles and fundraising for the Sterling Community Center.

Trail races of 70 mile, 30 mile and half marathon distances along the rugged, largely unsupported Shawangunk Ridge near Rosendale NY.

A 56 mile end to end run along the Farmington Canal Heritage Trail from West Suffield to New Haven raising funds for Mental Health Connecticut.

September 12, 2026 trail races in Pittsfield State Forest offering 50K, 25K, 15K and a new 5 mile option with proceeds supporting Free to Run.