Trail Running calendar near Danbury 2026-2027

Sterling Down & Dirty 5K is an annual family friendly obstacle race on Stratford Short Beach each September. Participants tackle more than 18 obstacles, join teams to fundraise for the Sterling Community Center, or volunteer on race day.

A multi-division trail event on the Shawangunk Ridge near Rosendale NY offering 70 mile, 30 mile and half marathon options on an unsupported, fully blazed route with shuttle access and finisher shirts and medals.

An urban obstacle race on the Jersey City waterfront on September 12, 2026. The event features a fast 3 mile course with 20 plus city-style obstacles, chip timing, new finisher medals, 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.

A group, end-to-end run along the Farmington Canal Heritage Trail from West Suffield to New Haven, roughly 56 miles, raising funds for Mental Health Connecticut. The route is largely flat and unsupported with a 14 hour completion cut off.

Trail race at Macedonia Brook State Park in Kent, Connecticut on September 13, 2026. Courses of 12K, 25K and 50K on single track forest trails with steep climbs, technical sections and cupless aid stations.

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

Timed trail events at Lakeside Park in Pawling, NY on a 1.68 mile mixed-surface loop offering 3, 6, 12 (day and night) and 24 hour races. The event is cupless, has an aid station and crew area, finisher medals, and buckles for 100+ miles.

A multi-day trail festival at Wawayanda State Park featuring a full range of distances from a kids 1 mile to a supported 100 mile event, on varied singletrack, boardwalk, and rocky terrain, with camping and community programming.

A trail event in Upper Nyack featuring 50 mile and 27 mile options on repeated 11.5 mile loops with significant elevation, three aid stations, and limited parking and lodging nearby.

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.

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 26 mile point to point trail race in the Slide Mountain Wilderness near Shandaken, New York, with nearly 7,000 feet of vertical gain over ridgelines and rocky terrain. Proceeds support Run Wild, Inc and there is a veteran and first respon..

Trail ultramarathon in Milford, PA on Sep 26, 2026, held on the McDade Trail through the Delaware Water Gap. Distances offered are 50K and 25K on a non-technical, rolling course.

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.