Trail Running calendar near Milford 2025-2026

TPK Bad Decisions is an exciting 30-hour team event held in Andover, NJ, where four-person teams tackle a series of mandatory challenges. This unique competition combines elements of adventure racing and problem-solving, requiring participants to navigate, carry heavy loads, and complete various tas..

The Red Wing Trail Challenge, organized by Conquer The World Endurance, is set for July 6, 2025, in Lagrangeville, NY. Participants can choose between a 60K race featuring approximately 6,600 feet of elevation gain and a 15K race with about 1,650 feet of gain. The event promises a scenic trail exper..

Pinky’s Rock n Rolla is a unique trail running event taking place in Richmond Hill, NY. This four-mile race offers participants the chance to experience actual trail running through the scenic Forest Park, featuring natural terrain shaped by glaciation. The event is designed for both newcomers and s..

The Blue Mountain Trail Run is a scenic 10K race set in the picturesque Poconos, specifically at the Blue Mountain Ski Resort. This event offers participants a unique opportunity to explore pristine singletrack trails that are typically inaccessible for obstacle courses, making it a favorite among t..

The Quadzilla 15K Trail Race, set in Schnecksville, PA, is known as Lehigh Valley's toughest trail race. The course features a diverse landscape, including rolling hills, water crossings, and single-track trails, providing a challenging experience for participants. Open to ages 13 and up, the race e..

The Squatchy Surprise is an exciting endurance event taking place at South Mountain Reservation in West Orange, New Jersey, on July 26, 2025. This unique trail running experience challenges participants to draw colored golf balls to determine which of four loops they will run, adding an element of c..

The Second Annual Orange Runners Club Summer Sizzle XC5k is set to take place at the Rich Furst Sanfordville Elementary School XC Course in Warwick, NY. This exciting event features a 5k run or walk, along with a Kids Dash, promoting teamwork, dedication, and fun in the spirit of cross country runni..

The Newbsanity Extreme Ravine Trail Race is an adventurous running event taking place in Binghamton, NY, featuring a challenging course designed for thrill-seekers. Participants can choose from three events: a 5K, a 15K, or a grueling 12-hour race. The course is set in the southern trail system of t..

The MCW Westfield Ultra is an annual running event hosted by MissionCleanWater at Tamaques Park in Westfield, NJ. Participants can choose to run for 3, 6, 9, 12, or 24 hours, completing as many laps as possible around a 0.8-mile loop. The event welcomes runners of all skill levels and includes a fun..

The Interstate 17 Trail Run, taking place in Closter, NJ, is a challenging 17-mile race designed for experienced runners. Participants will navigate a rugged course featuring over 5,000 feet of elevation change, with stunning views along the Hudson River. The race consists of four loops, including a..

Climb It For Climate is an exciting running event set in the picturesque Catskill Mountains at Belleayre Resort. Participants can choose between a challenging 25K or a shorter 8K course, both offering stunning views and a chance to connect with nature. This event emphasizes sustainability, operating..

The Thunder Chicken Squatch is an exciting trail running event taking place at Stokes State Forest in Branchville, NJ. Scheduled for August 10, 2025, participants can choose from various distances, including a 17-mile race, a 10K, and a 5K, with special categories for rucking. The event honors milit..

The Fabulous Fahnestock Trail Races, held in Fahnestock State Park, NY, offer a unique trail running experience with courses ranging from 5.5 miles to 50K. Participants can enjoy a mix of runnable dirt roads and challenging technical single track, making it suitable for both novice and experienced r..

The Dirty Dozen 50K is an ultra-running event set in New York City, challenging participants to complete a grueling 50-kilometer race consisting of 12 hilly loops in Forest Park. This event is designed for those who seek both physical and mental challenges, making it one of the tougher ultra-races i..

The Barn-B-Q Trail Festival is a unique outdoor celebration held at the restored Masker's Barn in Berkeley Heights, NJ. This event combines trail running and hiking with a lively barn party featuring BBQ, beer, wine, and various activities. Participants can enjoy self-guided trail tours, lawn games,..

The Salt Springs Field, Forest & Falls Trail Race is a challenging and scenic trail running event taking place in Montrose, Pennsylvania. Celebrating its 13th year in 2025, participants can choose from three race distances: 5K, 10K, and 50K. The courses traverse technical trails through an old-growt..

The FallApple event in South Orange, NJ, is a diverse running competition scheduled for September 6, 2025. Participants can choose from various distances, including a 5K, 10K, half marathon (13.1 miles), marathon, 50K, and 50 miles. The course features a mix of fire roads, single-track trails, hills..

The Macedonia Trail Race, organized by Steep Endurance, is an annual trail running event held in Macedonia Brook State Park near Kent, Connecticut. Now in its seventh year, the race offers three distances: 12K, 25K, and 50K, featuring challenging climbs, technical single-track trails, and scenic vie..

The Pawling 24 Hour Trail Running Festival is an exciting endurance event taking place in Pawling, NY, featuring a variety of race options including 24-hour, 12-hour, 6-hour, and 3-hour challenges. Participants will navigate a scenic loop course that combines pavement, grass, and single-track trails..

The Shawangunk Ridge Trail Run (SRT) is an exciting trail running event that showcases the stunning landscapes of the Shawangunk Mountains in New York. Participants can choose from three divisions: a 70-mile ultra, a 30-mile run, and a half marathon, catering to various skill levels. The event empha..