Trail Running calendar near Cheshire 2026-2027

A family friendly 5k obstacle race at Stratford Short Beach on September 5, 2026, featuring more than 18 obstacles with sand and water elements. The event raises funds for Sterling Community Center programs and supports team and individual..

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

A trail event in Rosendale, NY on the Shawangunk Ridge Trail offering 70 mile, 30 mile, and half marathon divisions. The course crosses varied terrain and is minimally supported so participants must carry food and water purification.

A seventh annual group run along the Farmington Canal Heritage Trail from West Suffield to New Haven to raise funds for Mental Health Connecticut. About 56 miles, largely self-supported with a 14-hour cut-off.

Trail race at Macedonia Brook State Park on 13 September 2026 featuring single-track forest trails, climbs, viewpoints and three distances: 50K, 25K and 12K.

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

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

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.

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.

This 5K trail run takes participants through the scenic trails and grasslands of Goddard Park in Warwick. The flat course is open to all ages and abilities. Registration includes a T-shirt and ample parking is available.

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

Run the Moosup Valley All Trail Race on September 27, 2026. Choose from a 5K, 8K, or 10K on the 100% trail course at Moosup Valley State Park. After the run, enjoy post-race food and a choice of a shirt or medallion.

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.

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.