Trail Running calendar near East Islip 2025-2026

The Pocantico Hills Marathon, held in Sleepy Hollow, NY, offers both marathon and half marathon distances through the scenic Rockefeller State Park. The single-loop courses feature rolling hills with picturesque views of the Hudson River and Palisades, passing fields, stone walls, bridges, lakes, st..

The Raven Rocks 10k Run is an annual trail race held at Ward Pound Ridge Reservation in Cross River, NY. Known for its challenging course, the race features rocky climbs, ridgeline trails, hilly meadows, ravines, and the historic fire tower site, offering scenic views of Long Island Sound, Connectic..

NYC Trail Mix is an annual ultra trail running event held in Staten Island, New York, featuring distances of 50 miles, 50K, and a half marathon. The course showcases over 35 miles of trails through the greenest parts of New York City, including Blood Root Valley, High Rock Park, La Tourette Park, an..

The Tarrywile Half Marathon, held in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the peaceful lakes within Tarrywile Park. Participants ca..

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 road and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are welcome, with a recommendation for some trail experience.Pa..

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 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 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 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..

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 consisting of two loops. The c..

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..