Trail Running calendar near Waterbury 2025-2026

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, following the scenic and flat Farmington Canal Heritage Trail from West Suffield to New Haven. This non-competitive challenge supports Mental Health Connecticut through fundrai..

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.

The Macedonia Trail Race is a rugged trail running event at Macedonia Brook State Park in Kent, CT, hosted by Steep Endurance. Now in its seventh year, it offers 12K, 25K and 50K distances on lush forest single-track with grinding climbs, technical descents, and several views. The 25K doubles the 12..

Winding Trails TRAIL RUNNING Series #3 is a Tuesday-night trail race series held at Winding Trails in Farmington, Connecticut. The 2025 edition runs five races from late August through late September, with participants choosing either a 5K or a 10K distance. Runners cover a roughly 3-mile loop on tr..

The Storybook Half Marathon is a scenic 13.1-mile trail race held in Roosevelt Forest, Stratford, Connecticut. The course consists of eight loops on a 1.64-mile wooded trail featuring singletrack and doubletrack paths with roots, rocks, and gentle hills, offering a charming yet moderately challengin..

Run for the Hills is the 4th Annual 5K trail run/walk held at the Oswegatchie Hills Nature Preserve in Niantic, CT. The route winds along hiking trails around the preserve’s perimeter, including a scenic stretch by Clark Pond, with exposed rocks and roots to challenge runners and walkers alike. Proc..

Located at Lakeside Park in Pawling, New York, the Pawling 24 Hour Trail Running Festival is the sixth edition of the endurance event, offering 24-, 12-, 6-, and 3-hour races (including a 12-hour night start). Runners tackle a 1.68-mile loop made up of pavement, grass, and single-track, with about 1..

The Wahaneeta Trail Run is a 5K trail race held in Westerly, Rhode Island, located on Moorhouse Road. Scheduled for September 13, 2025, it is the first event in the WTAC Fall Trail Race Series, which includes four races with a discount for registering in multiple events. This race embraces an "old s..

PCS Harvest Hustle 5K & Kids Run is a fundraising event at Pomfret Rec Park in Pomfret Center, CT, benefiting the Pomfret Community School PTO. It offers a Kids Fun Run and a trail 5K. The 5K winds through the Pomfret Forest on a technical, single-track wooded trail—rocky with roots and ups and down..

Shawangunk Ridge Trail Run (SRT) unfolds along the Shawangunk Ridge in the Hudson Valley, offering three divisions: 70-mile, 30-mile, and 1/2 marathon, spanning from High Point Monument in NJ to Rosendale, NY. The route winds through hills, wetlands, pine barrens, sky lakes, waterfalls, and conglome..

Where the Pavement Ends Single & Double Loop is a Ridgefield, Connecticut trail race that starts and finishes at Lake Windwing ballfields. The event offers two courses: a 4.25-mile Single Loop and an approximately 8-mile Double Loop. Runners traverse Hemlock Hills and Pine Mountain Open Space, with..

Winding Trails TRAIL RUNNING Series #4 is a five-race Tuesday-night trail series in Farmington, CT. Race #4 runs from Aug 26 to Sep 23, 2025, offering 5K or 10K options on a roughly 3-mile loop. Check-in and a rolling start take place at Winding Trails, 50 Winding Trails Drive.Registration is availa..

The Charlie Stavros Memorial Beach Run is a free, 3-mile race held at Westerly Town Beach in Westerly, Rhode Island. Organized by the Westerly Track Club and the Stavros family, this event takes place at low tide, featuring a scenic out-and-back course of 1.5 miles each way along the beach. The run..

Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey. The event offers a true Trail Festival with distances spanning from a 1-mile kids race to 100 miles, plus 100K, 50 miles, 50K, and a 36-hour format (with lightweight and heavyweight rucking divisions). The course co..

Angevine Farm Half Marathon takes place in Warren, CT, at Angevine Farm as part of the Angevine Farm Trail Festival. The course starts at the farm, loops on farm trails, enters Wyantenock State Forest and the Mattatuck Trail, delivering mostly technical but runnable single- and double-track terrain..

The Gardiner Dump Run is a scenic trail running event held in Gardiner, New York, featuring a 5k race with an option to complete two laps for a 10k distance. The course winds through single-track trails along wooded hillsides near the Wallkill River and untamed fields at Gardiner’s Riverbend Trails,..

The Cockaponsett Trails to a Cure is a trail running event held in Chester, Connecticut, within the Cockaponsett State Forest. Participants can choose between a 4-mile or a 9-mile race, with the shorter distance covering the first part of the longer course. The trail features natural terrain includi..

Winding Trails TRAIL RUNNING Series #5 is a Tuesday night event at Winding Trails in Farmington, Connecticut. The 2025 edition runs five races from August 26 through September 23, with a choice of 5K or 10K on an approximately 3-mile loop. Check-in and rolling start occur in the early evening at 50..

The Caldwell Cougar Chase XC 5K & 8K is a cross-country running event held at Garret Mountain Reservation in Woodland Park, New Jersey. Scheduled for September 26, 2025, it features a women's 5K and a men's 8K race on a rolling course that includes trails, hills, gravel, dirt paths, grass sections,..

The Cat's Tail Trail Marathon is a challenging 26-mile point-to-point trail race held in the Slide Mountain Wilderness Area of the Catskill Mountains, New York. Featuring nearly 7,000 feet of elevation gain, the course offers rugged terrain with rocky, technical climbs and descents, alongside stunni..