Trail Running calendar near Bridgewater 2026-2027

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 7000 feet of elevation gain. Multiple aid stations, finish-line food and race prizes, with proceeds supporting the land conservation nonprofit Run Wild, Inc.

Trail races of 50K and 25K run along the McDade Trail through the Delaware Water Gap near Milford, PA on Sep 26, 2026. The course mixes cinder path and singletrack; entries include a finishers item and post-race food.

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

Experience a scenic trail run through wooded hillsides and fields near the Wallkill River. Choose between a 5k or 10k race on single track trails and participate in the local athletic 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 loop ultra at Roosevelt Forest in Stratford CT offering distances from marathon to 100 miles. The 2.23 mile loop includes roots, rocky terrain and a larger hill, with the pavilion as the sole aid station and a 50 runner 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.

Experience an old school trail race along the historic Nipmuck Trail in Connecticut. This 26.4 mile double out and back event follows the blue blazed trails through challenging New England terrain.

Experience the wooded trails of Irvington during this four mile race. Navigate a course featuring elevation changes and natural turns through the local forest landscape.

A multi-distance trail event in Rocky Point, NY set on a 10.48 mile loop through Long Island pine barrens. Distances range from 10 miles to 150 miles with two staffed aid stations and support for pacers and crews.

A trail 5K and 1 mile accessible run in Wilton, CT on 10/10/2026 with participant T-shirts, on-site food and entertainment, spectator options, and sponsor levels; proceeds support the Prospectors mission for employment opportunities.

Experience a premier 13.1 mile trail race through the woods of New Rochelle. This half marathon takes runners across local trails for a focused off road experience in New York.

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.

Experience a point to point trail race in Northeast Connecticut on the Airline Trail. Choose between marathon, half marathon, and 10K distances with individual or relay team options to support local student education.

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.