Trail Running calendar near Milford 2025-2026

The WXT Ultra is a trail running event held in Titusville, New Jersey, starting and finishing at Washington Crossing Park. It offers two distances: a 25K and a 50K. The 25K course features mostly single-track trails, including an 8.5-mile section within the park and short road segments.The 50K follo..

The Camp Lackawanna Trail Challenge is a trail running event held in Tunkhannock, Pennsylvania, featuring 6-hour and 12-hour race options. Participants run on scenic trails starting from 1219 Vosburg-Neck Road, offering a challenging and immersive outdoor experience. The event emphasizes endurance a..

The Fall Back Into The Trails Series is an annual trail running event held at Red Wing Recreation Area in Lagrangeville, NY. The 2025 edition features three race distances: a challenging 100K (10 loops of 10K each with about 1000ft elevation gain per lap), a 50K (5 loops of 10K with approximately 50..

The Long Run - Fall Back is a trail running event held at Jacobsburg State Park in Wind Gap, Pennsylvania. Participants can choose from a 5-mile loop, a 3-hour, or a 6-hour timed event, running a course featuring approximately 450 feet of elevation change on single track and gravel trails. This edit..

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, Connecticut. The race features a rolling country course with an approximately 4-mile loop combining single track and farm trails, offering a scenic and community-focused atmosphere. Participants can choose..

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 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 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 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 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..