Trail Running calendar near Wading River 2026-2027

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.

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.

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.

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.

A 3.5 mile trail run and walk on the scenic, flat Mill Pond Trail at Woodtick Recreation in Wolcott CT on October 17, 2026. Tiered online registration is available and a post-event meal is included with registration.

A fall trail running event at Harriman State Park on October 18, 2026 offering a technical **13.1M** and a hilly **10K**, with marked singletrack, two aid stations for the half, a five hour finish cutoff, and limited field size.

An off road 50k through interconnected woodland preserves in southern Connecticut, featuring rolling forest roads and rocky single track. The event is nonprofit and proceeds support local land conservation, with volunteer roles for aid stat..