Trail Running calendar near Waterbury 2025-2026

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-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 an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event offers participants a scenic course around Clark Pond and through over 450 acres of coastal forest, showcasing the preserve's natural beauty. It serves as a fundraise..

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..

The PCS Harvest Hustle 5K & Kids Run is a community-focused event held at Pomfret Rec Park in Pomfret Center, Connecticut. It features a 5K trail run and a kids' fun run of half a mile, supporting the Pomfret Community School Parent Teacher Organization. The PTO uses funds raised to enhance educatio..

The Shawangunk Ridge Trail Run (SRT) is a challenging trail running event held in Rosendale, New York, featuring three race distances: a 70-mile ultra, a 30-mile race, and a half marathon. The course follows the scenic 70-mile Shawangunk Ridge Trail, which stretches from High Point State Park in New..

The Where the Pavement Ends Single & Double Loop is a trail running event held in Ridgefield, Connecticut, starting and finishing at the Lake Windwing ballfields. Scheduled for September 14, 2025, the race offers two options: a 4.25-mile single loop and an approximate 8-mile double loop through the..

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..

The Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey, offering a variety of trail running events over September 20-21, 2025. Distances range from a 1-mile kids run to a challenging 100-mile ultramarathon with a generous 36-hour cutoff, making it ideal for first-tim..

The Angevine Farm Trail Festival, held annually in Warren, Connecticut, offers a scenic and challenging trail running experience through grassy fields, land trust trails, state forest paths, single track, and dirt roads. The event features multiple distances including a half marathon, a new 8-hour r..

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..

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..

The Front Runners New York Cross Country 5K is an annual running event held at Van Cortlandt Park in the Bronx, New York. Celebrating its 22nd year in 2025, the race offers a scenic 5K cross-country course through the park's fall landscape. Participants meet at the iconic Tortoise & Hare Sculpture f..

The Moosup Valley 5K and 10K All Trail Race takes place in Moosup, Connecticut, on the newly restored Moosup Valley State Park Trail. This event features a 5K, a 10K, and a Kids Fun Run, all held on a 100% trail course that crosses only one dead-end road. The race starts and finishes at the Griswold..

The IronHike Endurance Series at Mohawk Mountain Ski Area in Cornwall, CT, is a multi-day endurance event held over four days in October 2025. Participants can choose from various challenges ranging from 12 to 84 hours, covering distances from 15 miles to over 150 miles with significant elevation ga..

The Run for the Pumpkins Trail Run, held in Westerly, Rhode Island at Bradford Preserve, is part of the WTAC Fall Race Series. This event features 5K and 10K trail races, along with a free 1K children's run for ages 10 and under. The courses highlight preserved town land and the Woody Hill Managemen..

The CFA Trail 5K & Children's Fun Run for Mental Health is a timed trail running event held at Deans Mill Farm in Stonington, Connecticut. Participants can choose between a 5K trail run or a fun run for children aged six and under. The race takes place amid beautiful fall foliage, offering a scenic..

The Run the Vineyards - Pindar Fall 5K and 8K is a scenic autumn race held at Pindar Vineyards in Peconic, NY, featuring courses through 300 acres of vineyard property. Participants can choose between a 5K and an 8K race, both on mostly flat, hard-packed dirt trails and short-cut grass, making the e..

The KMT Fall Foliage Frenzy is a timed trail running event held in Montebello, NY, featuring 3-hour and 6-hour race options. Participants run on a challenging 2.33-mile loop course in Kakiat Park, adjacent to Harriman State Park, with approximately 660 feet of vertical gain per lap. The course offer..