Trail Running calendar near Billings 2026-2027

A trail event at Nyack Beach State Park offering a 50 mile ultra with about 9,700 feet of ascent and a 27 mile mountain marathon with about 4,900 feet, on looped singletrack with river views.

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.

A community 5K run and a children’s 1 mile fun run at Schodack Town Park on September 19, 2026, raising funds for Hope House. Entry fees include 5K $30 and children free with parents running $30.

Trail races in Ridgefield CT offering a single loop of about 4.25 miles or a double loop of about 8 miles through Hemlock Hills and Pine Mountain. The technical, rocky course starts and ends at the Lake Windwing ballfields.

A 5K trail run at Winding Trails in Farmington on the designated course around Walton Pond, with registration from February 20 to September 20 and a $35 fee; overall and age-group awards plus a prize for the first local finishers.

Experience the technical terrain of Cockaponsett State Forest with 4 and 9 mile trail races. Navigate hills and rocky paths in Chester to support PanCAN and the Blue Blazed Trail Race series.

A timed charity tower climb at Empire State Plaza in Albany that reaches the 42nd floor with 809 steps. Water stations, bailout floors and medics are provided; registered participants receive a t shirt and finisher's medal.

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.

A trail running event in Gardiner, NY offering a 5 km run, an optional 10 km two-lap route and a 200 yard kids run, with pre registration T shirt incentives and a sneaker recycling program.

A scored 5K cross country race at Van Cortlandt Park in the Bronx on September 27, 2026, part of NYRR's fall series; includes free youth races for ages 2 to 18 and awards for top finishers across divisions.

Experience a massive endurance test at Mohawk Mountain Ski Area. This ultra trail event features a 152 mile course with over 72,000 feet of elevation gain to be completed within 84 hours.

Test your limits on a flat one mile loop at the Sussex County Fairgrounds. Choose from 6 to 72 hour timed races or certified marathon and 50K distances with full kitchen and shower access.

A 15 mile trail event at Mohawk Mountain Ski Area in Cornwall, Connecticut on October 3–4, 2026, offering 7,140' of elevation gain and a 12 hour time limit. Participants may run, hike, or walk; the event is produced by a veteran owned compa..

A 30 hour trail ultra at Roosevelt Forest with a 2.23 mile loop, marked course, multiple distance options, and a 100 mile finisher buckle. Aid is centered at the pavilion and one registered pacer is allowed per runner.

A timed endurance run in Cohoes, NY on October 3, 2026 offering 6 hour, 3 hour, 1 hour and relay options while supporting Flutters of Hope, a nonprofit for those affected by eating disorders.

Run through 300 acres of scenic vineyards on a flat trail course in Peconic. Enjoy live music, food trucks, and a post-race glass of wine at this chip-timed autumn event.

A four mile trail race through Irvington Woods on October 4, 2026, with varied terrain including climbs and stairs; start and finish at Irvington High School. Registration runs March 15 to September 4 with a $40 fee.

The Haystack Mountain Challenge on October 4, 2026, features a 5K, 10K and a half marathon across Barbour Woods and Haystack Mountain, with steep climbs, private trail sections, a cupless policy, water stations and on site refreshments.

A 13.7 mile trail race in Cold Spring, NY on October 4, 2026, featuring about 4,000 ft of climbing through the Hudson Highlands during peak foliage. The event is an UTMB Index Race and supports the NYNJTC.