Trail Running calendar near Billings 2026-2027

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 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.

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.

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 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..

A 50K looped trail race in Forest Park, Queens on August 29, 2026. Runners complete twelve 2.5 mile laps on the Orange Trail with about 300 ft of climb per lap and an 8 hour cutoff.

Barn B Q Trail Festival on Saturday 9/5/2026 at Masker's Barn pairs a trail run or hike with a five hour barn party featuring BBQ, drinks, music and games. Ticket options cover adults, designated drivers, and children.

A family friendly beach 5k obstacle race in Stratford each September, featuring 18 plus obstacles and community fundraising for Sterling Community Center programs. Participants and teams raise funds while running, walking, or navigating obs..

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.

City Challenge Race returns to Jersey City on September 12, 2026 with a fast 3-mile urban obstacle course featuring 20+ city-style obstacles, new finisher medals, professional chip timing, awards and free race photos.

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

An unsupported, end-to-end group run of about 56 miles along the Farmington Canal Heritage Trail from West Suffield to New Haven, organized as a fundraiser for Mental Health Connecticut with a 14 hour completion limit and required self-supp..

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.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.

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..

A three-day trail festival at Wawayanda State Park with events from a 1 mile kids race to a 100 mile race with a 36 hour cutoff, varied terrain, on-course aid support, free weekend camping and a program of panels and a film screening.