Trail Running calendar near Upper Nyack 2025-2026

The Red Wing Trail Challenge, held at Red Wing Recreation Area in Lagrangeville, NY, offers two trail race distances: a challenging 60K with approximately 6,600 feet of elevation gain, and a 15K featuring about 1,650 feet of gain. The 60K consists of four laps of a 15K loop that includes varied terr..

Pinky’s Rock n Rolla is a unique 4-mile trail race held in Richmond Hill, New York, featuring actual hiking trails rather than bridle paths or gravel roads. The course, located in Forest Park, offers a challenging and scenic run through naturally carved terrain shaped by glaciation, including a 100-..

The Second Annual Orange Runners Club Summer Sizzle XC5k is a cross country running event held in Warwick, New York, at the Rich Furst Sanfordville Elementary School XC Course. This 5k race, rooted in teamwork, dedication, competition, and fun, takes place on a course known for its rich cross countr..

The Squatchy Surprise is a unique trail running event held at South Mountain Reservation in Millburn, New Jersey, on July 26, 2025. Featuring 12-hour, 6-hour, and 3-hour options, the race challenges participants' endurance and strategy with a twist: runners draw colored golf balls before each loop t..

The MCW Westfield Ultra is an annual endurance running event held at Tamaques Park in Westfield, New Jersey. Participants can choose from 3, 6, 9, 12, or 24-hour race durations, aiming to complete as many laps as possible on a 0.8-mile loop featuring both pavement and gravel surfaces. The race offer..

The People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. It features a challenging 7-mile course through scenic forest trails, offering runners a chance to experience natural beauty and varied terrain. The race is part of the USATF Connecticut Mountain..

The Running Wild at Wildwood is a 2.5-mile trail run/walk held at Wildwood State Park in Wading River, New York. This scenic event takes place rain or shine, offering participants a chance to enjoy the natural beauty of the park while running or walking a well-marked trail. Amenities include live re..

The Thunder Chicken Squatch is a trail running event held at Stokes State Forest in Branchville, New Jersey. Scheduled for August 10, 2025, it offers multiple race distances including a challenging 17-mile run, a 10K, and a 5K, with additional 10K rucking divisions featuring lightweight (15 lbs) and..

The Interstate 17 Trail Run in Closter, NJ, is a challenging 17-mile race featuring over 5,000 feet of elevation change. Set along rugged, technical trails with stunning views of the Hudson River from New Jersey to New York, the course includes a mile out-and-back on a closed road followed by four l..

Climb It For Climate is a mountain trail running event held at Belleayre Mountain Ski Center in the Catskill Mountains, New York. Participants can choose between a challenging 25K course, approximately 15 miles with 5,000 feet of elevation gain and descent, or a shorter 8K course of about 5 miles wi..

The Tappen Brook 5K, held in Bridgewater, Connecticut, is an annual trail running event hosted by the Bridgewater Land Trust and the Bridgewater Recreation Commission. Set in the scenic Bridgewater Town Park, the course features newly developed trails winding through forested woodlands with gentle h..

The Fabulous Fahnestock Trail Races, held in Cold Spring, NY, offer runners a choice of 50K, 25K, and 5.5-mile distances through scenic Fahnestock State Park in the Hudson Valley. The course features a mix of runnable dirt roads and technical single-track trails, with challenging climbs, flowy desce..

The Hook Mountain Ultra is a challenging 51.7-mile trail run held in Upper Nyack, New York, featuring 10,928 feet of elevation gain. The course includes one 5.7-mile small loop followed by four 11.5-mile big loops, all starting and finishing at Nyack Beach State Park. Runners begin with a steep 1.6-..

The Dirty Dozen 50K is a challenging ultramarathon held in New York City, featuring a 50-kilometer distance composed of 12 hilly loops in Forest Park. Known as one of the tougher ultra-races in the city, it tests both physical endurance and mental toughness. The course's repetitive loop format and e..

Raptor Ridge Presented by Peace, Love, Trails (formerly the Sanctuary 6.5) is a challenging 6.5-mile trail run held at the scenic Westmoreland Sanctuary in Mount Kisco, New York. The race takes participants through the sanctuary's beautiful and rugged trails, spanning 669 acres with 8.5 miles of hik..

The Barn-B-Q Trail Festival, held in Berkeley Heights, New Jersey, is a unique outdoor event combining trail running or hiking with a lively barn party. Set in the historic Deserted Village of Feltville within Watchung Reservation, participants can enjoy self-guided trail tours ranging from 2 to 6 m..

The FallApple is a trail running event held in South Orange, New Jersey, at South Mountain Reservation. Scheduled for early September, the race offers a variety of distances including 5K, 10K, half marathon, marathon, 50K, and 50-mile options. The course features a mix of fire roads, single-track tr..

The Macedonia Trail Race, held in Macedonia Brook State Park in Kent, Connecticut, offers a unique trail running experience with lush single-track forest trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain with views of the Catskill Mountains. Now in its 7th ye..

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-tr..

The Shawangunk Ridge Trail Run (SRT) is a challenging trail running event held in Rosendale, New York, featuring three race distances: a 70-mile ultra, a 30-mile race, and a half marathon. The course follows the scenic 70-mile Shawangunk Ridge Trail, which stretches from High Point State Park in New..