Trail Running calendar near Milford 2025-2026

The Big Bear Squatchtoberfest is a challenging trail running event held at Harriman State Park in Tuxedo, New York. Organized by Sassquad Trail Running in partnership with the New York-New Jersey Trail Conference, it features a half marathon (13.1 miles) and a 10K race. The courses are technical wit..

The Hot Chili Challenge is a trail running event held in Andover, New Jersey, featuring an 8-mile trail run, a 5K run for adults, and a Kids Fun Run for ages 5-12. Participants in the adult races receive t-shirts, hobo bags, and finisher medals, while kids receive finisher medals. Awards and swag ar..

The Camp Lackawanna Trail Challenge is a trail running event held in Tunkhannock, Pennsylvania. Participants can choose between 6-hour and 12-hour race options, testing endurance on scenic trails. The event takes place at 1219 Vosburg-Neck Road and offers a challenging course through natural terrain..

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 begin..

The WVS Fall Trail Run will take place in Wyoming on Sunday 26 October 2025. You can run 5 miles.

The Fall Back Into The Trails Series, held at Red Wing Recreation Area in Lagrangeville, NY, offers challenging trail races including a 100K, 50K, and 10K. The 50K consists of five 10K loops with approximately 5,000 feet of elevation gain, while the 100K features ten 10K loops with about 1,000 feet..

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 a mix of single track and gravel trails...

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 that includes single track and farm trails, offering a scenic and community-focused atmosphere. Participants can cho..

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

The Raven Rocks 10k Trail Run is an annual challenging trail race held at Ward Pound Ridge Reservation in Cross River, NY. The course features rugged terrain with rocky climbs, ridgeline trails, hilly meadows, and ravines, ascending to the park's two highest points: Raven Rocks Overlook and the Fire..

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 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 park's tranquil lakes. The event fe..

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, offering a community-focused a..

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 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 also choose a 5k distance or a virtual race option.Runn..

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 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. Scheduled for January 31, 2026, this 9th edition offers participants options to run or hike a 5K loop, or join timed 3-hour and 6-hour challenges, including a new rucking di..

The Mahlon Winter Donut Trail Run will take place in Lake Hopatcong on Sunday 8 February 2026. You can run between 5 and 13 miles.