Trail Running calendar near Windham 2026-2027

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 race at Clapp Park in Pittsfield, MA on a certified .355 mile loop with chip timing, bottle drop aid, age group awards, and proceeds benefiting the AYJ Fund. A virtual option may be available.

The 3rd Annual Tappen Brook 5K in Bridgewater, CT on August 9, 2026 runs on the new Bridgewater Town Park trails through woodlands near Lake Lillinonah, with participation gifts and awards for top finishers.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026 with 50K, 25K and a 5.5 mile option, multiple aid stations, a post race meal and proceeds supporting park 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 mountain trail event at Belleayre Resort offering a 25K (about 16 miles, 5000+ ft elevation change) and an 8K on ski slopes; both distances allow hikers. The event is organized as zero carbon and raises donations for The Catskill Center.

Jug End Loop Ultra on August 22, 2026 at Jug End State Reservation in Egremont, MA features a 4.2 mile loop through woods, fields and an apple orchard. Participants run as many 4.2 mile laps as they choose within six hours and receive award..

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 5K trail fun run through the hills of Butternut Valley in Garrattsville, NY on August 22, 2026, presented by Butternut Valley Alliance as part of the Butternut Valley Days celebration; registration fee is $35.

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..

A 50K trail ultramarathon near Stony Creek, NY on September 6, 2026, with a lollipop course from Harrisburg Lake through Wilcox Lake Wild Forest, multiple aid stations, and about 3,028 feet of elevation change.

A trail race along the scenic Shawangunk Ridge near Rosendale NY offering 70-mile, 30-mile, and half marathon divisions on an unsupported, checkpointed route with shuttle access and event swag.

Trail races in Pittsfield State Forest on September 12, 2026 include a 50K ultramarathon and shorter looped options on a course with significant climbing and three aid stations. Proceeds support Free to Run Inc.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

Trail races in Brookfield New York offer a 5k, 15k and a 50k ultra on truck and horse trails; the 50k includes 4,800+ feet of vertical gain and a nine hour cutoff.

A timed trail festival in Pawling, NY offering 24, 12 (day and night), 6 and 3 hour events on a roughly 1.7 mile loop with about 160 feet of gain per loop. The event includes an athlete tent area, aid station offerings, cupless rules, and f..

Trail run and walk at Huyck Preserve in Rensselaerville NY on Saturday September 19 2026. Routes of 2 5 and 8 miles pass Lake Myosotis and a historic racetrack while raising funds for local organizations.

Hope House 5K Trail Run and Walk for Recovery on September 19, 2026 at Schodack Town Park includes a 5K run or walk and a children's 1 mile fun run. Proceeds support Hope House services for people affected by substance use disorder.

A 26 mile point to point trail race in the Slide Mountain Wilderness with nearly 7,000 feet of vertical gain. Multiple aid stations, post race refreshments, and proceeds support Run Wild, Inc.

50K and 25K trail races on the McDade Trail in Milford, PA, starting at Smithfield Beach. The out and back route is mainly rail trail cinder with three aid stations and a cupless policy.