Trail Running calendar near Danbury 2026-2027

The Where the Pavement Ends trail race offers a technical 4.25-mile single loop or an 8-mile double loop through the Hemlock Hills. It's part of the multi-race Trail Mix Series. Both races start and finish at the Lake Windwing ballfields in..

Run a scenic 5K trail race through 300 acres of natural terrain at Winding Trails in Farmington. Compete for age group awards and the local Lee Chisholm Award on a course surrounding Walton Pond.

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.

A point-to-point, rugged trail marathon with nearly 7000 feet of elevation gain in New York's Catskill Mountains. The route features technical climbs, scenic views, and multiple aid stations, with proceeds supporting land conservation.

Run the scenic McDade Trail through the historic Delaware Water Gap. The non-technical, rolling course is a mix of cinder path and singletrack. Each entry includes a finisher's item and supports trail maintenance.

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

The Gardiner Dump Run offers 5k and 10k trail races through the scenic Riverbend Trails. The course winds along wooded hillsides and fields near the Wallkill River. Day-of registration is available, and the event features a sneaker recyclin..

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.

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.

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.

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.