Trail Running calendar near Stratford 2026-2027

IronHike Endurance Series runs October 1 to October 4, 2026 at Mohawk Mountain Ski Area in Cornwall CT. The series offers multiple ultra trail events from about 61 miles to 152 miles with large elevation gains and run, hike or walk options.

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.

The Run for the Pumpkins Trail Run will take place in Westerly on Saturday 3 October 2026. You can run between 5 and 10 kilometers.

Run an 8K or 5K through the autumn scenery of Pindar Vineyards on a flat trail course. Your entry includes chip timing, a tech shirt, and a post race party with wine, music, and food. The event supports the NY Cancer Foundation.

The NipMuck Trail Marathon is a classic 26.4-mile race on Connecticut's rugged Nipmuck Trail. Runners can also team up for a two-person relay. The event supports local trail programs through the nonprofit Shenipsit Striders running club.

Event Overview The Tesla Hertz Run is a multi-distance trail running event held in Rocky Point, New York, on Long Island. The races take place over a weekend in early October. Participants can choose from several distances, with specific st..

Challenge your legs on the slopes of Mohawk Mountain Ski Resort in Cornwall, CT. Choose from marathon, half marathon, 10K, or 5K distances on a course featuring climbs, descents, and fall foliage views. Hikers are welcome on the shorter tra..

A single-loop half marathon through five parks in lower Westchester County, New York, starting at the Thomas Paine Cottage and finishing at New Rochelle High School. Mostly shaded dirt trails with varied wildlife and published race results.

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.

A scenic multi-distance running event on Long Island featuring a marathon crossing the Robert Moses Causeway. Run for a cause as all proceeds go to support local veterans services.

Experience the quiet solitude of Northeast Connecticut in this point to point race featuring marathon, half marathon, and 10K distances for individuals and relay teams.

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.

Tackle the technical trails of Harriman State Park at the Big Bear SquaTCh South. Choose a challenging half marathon or 10K on a scenic loop with significant elevation gain. Your registration supports local trail maintenance, and the event..

This Halloween-themed run on New Jersey's legendary Clinton Road offers a spooky adventure. Participants can choose from a Zombie Crawl, a 5k, or a 10k, all featuring zombie volunteers and a festive finish line celebration.

The Grills Trail Run will take place in Westerly on Saturday 24 October 2026. You can run between 10 and 10 miles.

Experience peak autumn foliage at the Mt. Tom Trail Race featuring a 25k solo or relay, a 10k, and a 5k fun run through rugged Massachusetts state park trails with significant elevation.

A 5 mile trail race at Muscoot Farm in Katonah, NY on October 25, 2026, with two kids races for specified age groups. Participants receive Farm Bucks for the farmers market; shirts are optional and ordered in advance.

The Fall Back Into The Trails Series returns to New York's Red Wing Recreation Area. Runners can tackle a 100k, 50k, or 10k on challenging, looped courses. All finishers earn a custom medal, and the ultras are UTMB Index races.

This 8-hour timed trail run takes place on the rolling farm trails at Gurski Farm in Brookfield, CT. Runners complete as many laps as possible on a course featuring single track. It offers a community atmosphere where participants frequentl..

Run through the historic carriage roads of the Rockefeller State Preserve in the Hudson Valley. The single-loop marathon and half marathon courses pass fields, stone walls, and scenic vistas without any pavement or cars. It's a walk-friendl..