Trail Running calendar near Bronx County 2025-2026

The Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is known as one of the toughest trail half marathons in the region. The challenging course features nearly 3,000 feet of elevation gain and technical Northeast single-track terrain. Runners enjoy stunning views of Danbury a..

The Fall Fling 400 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. It features two main races: a 400-minute timed event where participants run as many loops as possible on a roughly two-mile trail course with varied terrain, including wo..

The Squatchy Leftovers Trail Race takes place at South Mountain Reservation in West Orange, New Jersey. Scheduled for November 29, 2025, it offers multiple distances: 50K, 25K, 10K, 5K, and a 1-mile kids run, all based on a 5K loop course. The trail features a mix of wide carriage roads and technica..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event not only..

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants can choose between 5k and 10k distances, both chip-timed, a..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Hamden, Connecticut, known for its stunning views and diverse trails. The race features a straightforward course on the Tower Trail, a smooth carriage road that climbs over 600 feet in 1.5 miles to the park's Obser..

The PPTC Endurance Fest is an ultramarathon event held in Brooklyn, NY, featuring 50-mile and 50-kilometer race options. The race takes place on a looped course within Prospect Park, consisting of 9 or 15 laps of a 3.33-mile loop. Starting and finishing near the Lincoln Road Entrance, the event hono..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5K race offers participants a chance to escape the road and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are welcome, with a requirement of some trail experience.Partic..

The Holmdel Classic is a challenging end-of-year trail race held in Holmdel Park, Monmouth County, New Jersey. Featuring a roughly 50K ultra and a half-distance option, the race consists of multiple loops on a 4.65-mile course with 95% trail terrain and 584 feet of elevation gain per lap. The course..

The Frosty Fat Sass is an annual trail running and hiking event held at South Mountain Reservation in West Orange, New Jersey. Participants can choose from a 5K loop, a 3-hour, or a 6-hour endurance challenge, with a new rucking division available for the 3-hour event. The course features a mix of w..

The Mahlon Winter Donut Trail Run & Hike features a scenic adventure through the beautiful trails of Lake Hopatcong, NJ. Scheduled for February 8, 2026, participants can choose from three distances: a 5-mile, 10-mile, or half marathon (13.1 miles). The courses offer a mix of terrain, including strea..

The Livingston Oval Ultra, held in Livingston, New Jersey, is a timed running event featuring 1-hour, 3-hour, 6-hour, and a new 12-hour race distance for 2026. Participants run laps around a USATF-certified, fast, and flat oval course, aiming to cover as much distance as possible within their chosen..

The Squatchapple Trail Race takes place at South Mountain Reservation in West Orange, NJ, offering distances of 11 miles, 20 miles, 50K, and 50 miles. The course features three loops of varying lengths (4, 5.5, and 7 miles) combining carriage roads, singletrack, and some road crossings, with signifi..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop with over 3,000 feet of vertical gain and a 50K option for those who want to complete..

Squatchywaska Mountainfest is a challenging trail running event held in Ellenville, New York, featuring two race distances: a 25K and a 10-mile course. Set in the stunning Shawangunk Ridge, runners navigate rugged mountain singletracks, cliffs, and glacially polished ledges through pitch pines, huck..

The Wawayanda Trail Fest, held in Hewitt, New Jersey, is a spring trail running event featuring distances of 100K, 50 miles, 50K, and a half marathon. The course offers a scenic 26+ mile loop through Northern Jersey's hills, including rhododendron tunnels, marsh bridges, gravel roads, and single-tra..

Leatherman's Loop is a renowned 10k trail race held annually each spring at the Ward Pound Ridge Reservation in Cross River, New York. Established in 1987, it is considered the largest trail race on the East Coast of the United States. The event features a challenging and scenic course through the r..

The Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event featuring 100K, 50-mile, and 50K distances. The course consists of rolling loops primarily on flat, paved roads around scenic Lake Waramaug, known for personal record performances. Runners enjoy..