Trail Running calendar near Billings 2026-2027

A point to point trail marathon in the Catskill Mountains with almost 7,000 feet of elevation gain, multiple aid stations, finishline food and proceeds that support land conservation. Registration opens May 1, 2026.

Trail races on the McDade Trail through the Delaware Water Gap on September 26, 2026. Distances are 50K and 25K with post-race food, a finishers item, and a portion of fees donated to trail maintenance.

The Front Runners New York Cross Country 5K will take place in Bronx County on Saturday 26 September 2026. You can run 5 kilometers.

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.

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.

This 24-hour trail challenge in Cornwall, CT, covers over 28 miles and 13,685 feet of elevation gain. Participants can run, hike, or walk the double marathon distance or tackle it as a relay.

A 30 hour looped trail ultra at Roosevelt Forest in Stratford, CT, run on a 2.23 mile lap with roots, rocks and a notable hill. Multiple distances are offered and awards are based on most miles completed during the time limit.

A fall endurance event in Cohoes, NY offering 6 hour solo and relay, 3 hour and 1 hour timed formats, with buckles for solo runners over 26.2 miles, swag and finisher awards, and fundraising for Flutters of Hope Inc.

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 4 mile trail race through the Irvington Woods on October 4, 2026, with varied terrain and stairs. Start and finish are at the back soccer field of Irvington High/Middle School; registration runs March 15 to September 4 with a $40 fee.

Trail races and a half marathon take place around Barbour Woods and Haystack Mountain in Norfolk, CT on October 4, 2026. Routes include single track and carriage roads and the half marathon features over 2000 feet of elevation gain.

A multi-day trail event near Rocky Point, NY, run on a 10.48-mile loop with distance options from 10 miles to 150 miles. Two staffed aid stations provide food and volunteer support; pacers and crews are allowed with prior notice.

Third annual trail event on October 10, 2026 in Wilton, CT featuring a 5K and a 1 mile accessible run/walk, with food and entertainment, supporting employment opportunities for people with disabilities.

A running race at Mohawk Mountain Ski Resort in Cornwall CT on October 11 2026, organized by Steep Endurance in cooperation with the ski area, with entry fees ranging from 30 to 95 USD.

A single-loop trail half marathon through five parks in lower Westchester County, New York, with most of the route on dirt under tree cover. Part of the Trail Mix Series and noted for varied wildlife along hidden trails.

Run or walk through the scenic trails of Blydenburgh Park this autumn. Participants enjoy a 5K trail course complete with seasonal treats and commemorative event swag.

Experience Long Islands scenic Robert Moses Causeway in this multi day running event. Support local veterans while choosing between marathon, half marathon, 10k, and 5k distances with finisher medals for all participants.

This 3.5-mile trail run/walk on the flat Mill Pond Trail happens in Wolcott, CT. The Wolcott Lions Club hosts the event, which includes a race t-shirt and clam chowder. Registration opens online with a lower early-bird rate.

A fall trail running event at Harriman State Park on October 18, 2026 offering a technical **13.1M** and a hilly **10K**, with marked singletrack, two aid stations for the half, a five hour finish cutoff, and limited field size.