Trail Running calendar near West Rock 2025-2026

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, and a 4-mile race consisting of..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course through the scenic park setting..

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 including a 50K (10 loops), 25K (5 loops), 10K (2 loops), 5K (1 loop), and a 1-mile kids run. The course features a 5K loop with a mix..

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 demanding 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 st..

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. This event honors New York City's road ultra heritage, following in t..

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 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 Squatchy Onesie Fest 5K is a fun and unique trail running event held at Ramapo Valley County Reservation in Mahwah, New Jersey. Participants are encouraged to wear their favorite onesies, adding a playful atmosphere to this winter race. The course is a scenic, mostly flat "lollipop" loop around..

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 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..

Run Across CT is a challenging ultramarathon spanning 123 miles across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The point-to-point course traverses 25 towns, combining approximately 57 miles of well-maintained trails with scenic backroads an..

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 new rucking divisions with lightweight (15 lbs) and heavyweight (30 lbs) packs, the course offers rugged, technical trails with steep..

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 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,..

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 set on a scenic 26+ mile loop course with rhododendron tunnels, marsh bridges, gravel road..

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..