Trail Running calendar near Chester 2025-2026

Located in Union, Connecticut, the Northern Nipmuck Trail Race is a 16-mile ultramarathon staged just outside Bigelow Hollow State Park. The course runs south on the Nipmuck Trail through the Yale-Myers Forest, crosses Barlow Mill Rd at mile 4, then reaches a turnaround at Boston Hollow before retra..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop featuring over 3,000 feet of vertical gain, and a 50K option consisting of two loops...

Run Across CT is an ultramarathon event featuring a 123-mile point-to-point course across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The route traverses 25 towns and combines approximately 57 miles of well-maintained trails with scenic backroa..

The John Jay Community Trail Race, held in Cross River, NY, is a competitive 5k run on the newly developed John Jay Community Cross Country Trail. The course begins on the lower fields of the John Jay Campus, quickly entering challenging, hilly wooded trails near the middle and high schools, and fin..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high demand, entry is determined by a lottery system.The registrati..

Jack Bristol Lake Waramaug Ultra Races run around Lake Waramaug in Kent, Connecticut, offering 100K, 50M, and 50K. One of the oldest ultras in the United States, it marks its 52nd anniversary in 2026 as part of the Mount to Coast 100K Series. The rolling, mostly flat course uses paved roads around t..

Breakneck Point Trail Runs, hosted by Red Newt Racing, take place at University Settlement Camp in Beacon, NY. The event offers two challenging distances: a half marathon of approximately 14.5 miles with 4,800 feet of elevation gain, and a full marathon of about 26.4 miles with 9,000 feet of gain. T..

Run The Farm is a trail-running event held at Muscoot Farm in Katonah/Somers, NY. The centerpiece is a 5-mile trail race through farm fields and woodlands, complemented by two Kids Run The Farm events for younger runners. The course highlights Muscoot’s rural scenery and woodland trails, creating a..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held in Mansfield, Connecticut, starting at Mansfield Hollow State Park. The course follows the scenic Nipmuck Trail alongside the Fenton River, featuring varied terrain including small bridge crossings, a climb to a 50-foot cliff, f..