Trail Running calendar near Bear Mountain 2026-2027

Timed trail races at Lakeside Park in Pawling, NY on an approximately 1.68 mile loop with 3, 6, 12 and 24 hour options, cupless format, aid station supplies, finisher medals and specific support and pacer rules.

A multi-day trail festival at Wawayanda State Park in mid-September 2026 featuring races from 1 mile to 100 miles, free participant camping, a 36 hour 100 mile option with a single late cutoff, and community mental health partnerships.

The Hook Mountain Ultra is a demanding 50-mile or 27-mile trail race in Upper Nyack, NY. The course features repeated loops with significant climbs, ridge running, and scenic Hudson River views. It includes full aid station support and has..

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..

Run a scenic 5K trail race through 300 acres of natural terrain at Winding Trails in Farmington. Compete for age group awards and the local Lee Chisholm Award on a course surrounding Walton Pond.

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.

The Caldwell Cougar Chase 5K and 8K will take place in Woodland Park on Friday 25 September 2026. You can run between 5 and 8 kilometers.

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 an ultimate endurance test at Mohawk Mountain by taking on 61 miles and 29,155 feet of elevation gain. Participants have 72 hours to run hike or walk their way to an Everest sized vertical achievement.

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.

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.

A trail event at Camelback Resort on a 2.5 mile loop with about 900 ft elevation per loop. Distances include Baby Basilisk, 5 mile, 10 mile solo and 10 mile relay, plus a ruck division and a cupless aid policy.

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.