Trail Running calendar near Cheshire 2026-2027

An unsupported, end-to-end group run of about 56 miles along the Farmington Canal Heritage Trail from West Suffield to New Haven, organized as a fundraiser for Mental Health Connecticut with a 14 hour completion limit and required self-supp..

Trail races in Pittsfield State Forest on September 12, 2026 feature 50K, 25K, 15K and 5 mile options. The double loop course includes long climbs, fast descents and three aid stations, with proceeds supporting Free to Run.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.

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

A free 3 mile out-and-back beach run at Westerly Town Beach held at low tide. The community event is organized by the Westerly Track Club and the Stavros family as a memorial run.

A timed trail festival in Pawling, NY offering 24, 12 (day and night), 6 and 3 hour events on a roughly 1.7 mile loop with about 160 feet of gain per loop. The event includes an athlete tent area, aid station offerings, cupless rules, and f..

A trail event at Nyack Beach State Park offering a 50 mile ultra with about 9,700 feet of ascent and a 27 mile mountain marathon with about 4,900 feet, on looped singletrack with river views.

A community fundraiser in Pomfret Center with a trail 5K and a 0.5 mile kids run supporting the Pomfret Community School PTO. Early and later registration fees differ and awards plus finisher medals are given.

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.

A 5K trail run at Goddard Park in Warwick, RI on September 26, 2026, with a bayside course and start and finish near the golf course clubhouse. Open to all ages, with published entry fee tiers and on site parking and facilities.

An all-trail event on the Moosup Valley State Park Trail in Moosup, CT offering 5K, 8K, 10K and a free Kids Fun Run with post-race shirts or medallions and food at Weidele's; proceeds benefit a local Rotary charity.

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.

A scored 5K cross country race at Van Cortlandt Park on Sunday, September 27, 2026, featuring varied trail terrain, live runner tracking, awards for top overall finishers, and a free Rising NYRR kids program for ages 2 to 18.

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.

A 24 hour trail event at Mohawk Mountain Ski Area in Cornwall Connecticut featuring a Double Kuwohi route of about 28 miles and 13,685 feet of elevation. Participants may run, hike, or walk.

A 30 hour trail ultra at Roosevelt Forest with a 2.23 mile loop, marked course, multiple distance options, and a 100 mile finisher buckle. Aid is centered at the pavilion and one registered pacer is allowed per runner.

Trail races at Bradford Preserve on October 3, 2026 feature 5K, 10K and a free kids run on dirt trails with seasonal course markings and a required orange clothing rule per state regulations.

A 5K fall trail run and walk at Ryan Park in North Kingstown on October 3, 2026, benefiting the North Kingstown Firefighters Association. Registrations before September 14 include a race day t shirt and top finishers receive medals.