Trail Running calendar near Cross River 2025-2026

Rob's Trail Run Edition is a trail running event held in Woodbury, New York, at Stillwell Woods Preserve. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those 18 and under. The c..

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 the iconic Sleeping Giant State Park in Hamden, Connecticut. The race features a simple yet challenging course on the Tower Trail, a mostly smooth carriage road that ascends over 600 feet in 1.5 miles to the park's Observation Tower, offering..

The PPTC Endurance Fest is an ultramarathon event held in Brooklyn, NY, featuring 50-mile and 50-kilometer race options. Taking place in Prospect Park, the course consists of multiple 3.33-mile loops—9 loops for the 30-mile race and 15 loops for the 50-mile race—starting and finishing near the Linco..

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 roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail experience.P..

The Holmdel Classic is a challenging end-of-year trail race held in Holmdel Park, Monmouth County, New Jersey. Featuring a 4.65-mile loop with 584 feet of elevation gain, the course covers diverse terrain including grass, dirt, rocks, roots, gravel, pavement, and varied inclines. Participants can ch..

The Frosty Fat Sass is an annual trail running and hiking event held in West Orange, New Jersey, at the South Mountain Reservation's Turtleback Rock Picnic Area. Scheduled for January 31, 2026, this 9th edition offers participants options to run or hike a 5K loop or take part in 3-hour or 6-hour tim..

The Mahlon Winter Donut Trail Run & Hike is a scenic trail running event held at Saffin's Pond in the Mahlon Dickerson Reservation, Lake Hopatcong, New Jersey. Scheduled for February 8, 2026, it offers three race distances: a 5-mile loop, a 10-mile course consisting of two loops, and a 13.1-mile hal..

The Squatchy Onesie Fest 5K is a fun and unique trail running event held at Ramapo Valley County Reservation in Mahwah, New Jersey. Participants complete a flat, scenic 1.6-mile "lollipop" loop around Scarlet Oak Pond twice to finish the 5K. The course features mostly wide gravel and dirt trails wit..

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..

Squatchapple is a popular trail running event held at South Mountain Reservation in West Orange, NJ, offering distances of 11 miles, 20 miles, 50K, and 50 miles. The race features a challenging course composed of three loops—4, 5.5, and 7 miles—with varied terrain including carriage roads, singletra..

The Mt. Tammany 10 is a challenging ultramarathon held in Delaware Water Gap, New Jersey, featuring an almost 40-mile course with over 10,000 feet of elevation gain. The race consists of 10 grueling loops, each involving a climb to the summit of Mt.Tammany via the Red-Dot trail, followed by a descen..

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 runners who complete two l..

Big Bear Squatch North is a challenging trail running event held at Harriman State Park in Bear Mountain, New York. Featuring a half marathon and 10K races, including a unique rucking division with lightweight (15 lbs) and heavyweight (30 lbs) categories, the course offers rugged, technical trails w..

The Spring SOMO Timed Trail Races take place at South Mountain Reservation in South Orange, New Jersey. This event features a looped trail course of 1.88 miles (just over 3K) that includes single track, pavement, and fire road sections. Runners can choose from multiple race options: 1 loop (3K), 2 l..

The John Jay Community Trail Race, held in Cross River, NY, is a competitive 5k run on the newly developed John Jay Community Cross Country Trail. The course begins on the lower fields of the John Jay Campus, quickly entering challenging, hilly wooded trails near the middle and high schools, and fin..

The Wawayanda Trail Fest is a challenging trail running event held in Vernon Township, New Jersey, at Wawayanda State Park. It features multiple distances including a 100K, 50 Mile, 50K, and Half Marathon, all running on a scenic 26+ mile loop course with rhododendron tunnels, marsh bridges, gravel..

The Squatchywaska Mountainfest is a challenging trail running event held in Ellenville, New York, featuring two distances: a 25K (approximately 17 miles) and a 10-mile race. Set in the scenic Shawangunk Ridge, runners traverse rugged mountain singletracks, including pitch pines, huckleberry bushes,..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high demand, entry is determined by a lottery system.The registrati..

The Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event celebrating its 52nd anniversary in 2026. It features three race distances: 100K, 50 miles, and 50K, all conducted on primarily flat, rolling loops around scenic Lake Waramaug on paved roads. The..