Trail Running calendar near Stratford 2026-2027

A community fundraiser at Pomfret Community School featuring a 5K trail run and a 0.5 mile kids fun run, with early and late registration tiers, age and gender awards, and finisher medals for all participants.

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.

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

Trail races on the restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a free Kids Fun Run, post-race food at Rotary Park, and proceeds supporting the Rotary Club of Plainfield Foundation.

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.

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 timed trail ultra at Roosevelt Forest on a 2.23 mile loop. Runners complete as many laps as possible with a pavilion aid station and awards based on most miles in 30 hours.

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.

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.

A 26.4 mile trail marathon on Connecticut's Nipmuck Trail featuring rocks, roots, mud and wood bridges, plus a two-runner relay option. The course uses a 13 mile segment with out-and-back sections and published cutoffs.

A 4 mile trail race through the Irvington Woods on October 4, 2026, with varied terrain and stairs. Start and finish are at the back soccer field of Irvington High/Middle School; registration runs March 15 to September 4 with a $40 fee.

Trail races and a half marathon take place around Barbour Woods and Haystack Mountain in Norfolk, CT on October 4, 2026. Routes include single track and carriage roads and the half marathon features over 2000 feet of elevation gain.

A multi day trail ultrarunning event near Rocky Point, NY on October 9 to 12, 2026. Runners use a 10.48 mile loop with two aid stations and a range of distances from 10 miles to 150 miles.

Third annual trail event on October 10, 2026 in Wilton, CT featuring a 5K and a 1 mile accessible run/walk, with food and entertainment, supporting employment opportunities for people with disabilities.

Trail races at Mohawk Mountain in Cornwall CT offer 5K, 10K, Half Marathon and Marathon routes with measured elevation gains, ski area trail loops, cupless hydration policy, and aid stations for longer distances.

A single-loop trail half marathon through five parks in lower Westchester County, New York, with most of the route on dirt under tree cover. Part of the Trail Mix Series and noted for varied wildlife along hidden trails.