Trail Running calendar near Woodbury 2025-2026

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 is a challenging 6.5-mile trail race held at the Westmoreland Sanctuary in Mount Kisco, New York. The event takes runners through the scenic and rugged trails of the 669-acre wildlife preserve, which spans three towns and offers 8.5 miles of hiking paths..

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 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, held annually in Macedonia Brook State Park in Kent, Connecticut, offers trail runners a unique experience with its lush forest trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on clear..

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..

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event features a scenic course that winds around Clark Pond and through over 450 acres of coastal forest, offering participants a beautiful natural setting. It serves as a..

The Storybook Half Marathon is a friendly trail running event held in Roosevelt Forest, Stratford, Connecticut. The course consists of 1.64-mile loops repeated eight times, totaling the half marathon distance of 13.1 miles. Runners, joggers, hikers, and walkers are all welcome, with a four-hour time..

The Mountain Lakes Trail Run & Walk in Princeton, NJ, is a scenic event held at the Billy Johnson Mountain Lakes Nature Preserve, benefiting the Friends of Princeton Open Space. It features a 5K+ trail run and a 3K walk, both traversing a mix of paved park trails, unimproved service paths, and singl..

The Wild Goose Trail Festival is a multi-day trail running event held at Wawayanda State Park in Hewitt, New Jersey. Taking place September 20-21, 2025, it offers a variety of race distances including a 1-mile kids run, 10K, half marathon, 50K, 50-mile, 100K, 100-mile, and a 36-hour timed event. The..

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

The Cockaponsett Trails to a Cure is a running event taking place in Chester, Connecticut, featuring two trail races: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The course includes challenging terrain with roots, rocks, and hills, and is designed to accommodate runner..

The Angevine Farm Trail Festival is a scenic trail running event held in Warren, Connecticut, in the state's picturesque northwest corner. The festival features multiple race options including an 8-hour endurance run on a 1.25-mile farm loop, a half marathon traversing grassy fields, land trust trai..

The Water Gap 50k and 25k is a scenic trail running event held in Milford, Pennsylvania, featuring distances of 50 kilometers and 25 kilometers. The race course follows the McDade Trail, a 32-mile route through the Delaware Water Gap National Recreation Area, known for its stunning views of the Dela..

The Front Runners New York Cross Country 5K is an exciting running and walking event scheduled to take place at Van Cortlandt Park in the Bronx on September 27, 2025. This event invites participants of all skill levels to enjoy a scenic course while promoting fitness and community spirit. The 5K run..

The IronHike Endurance Series is a unique multi-day event taking place at Mohawk Mountain in Cornwall, CT, from October 2 to October 5, 2025. Participants can choose from various challenges, including individual and team formats, with distances ranging from 15 to over 152 miles, featuring significan..

The NJ Trail Series One Day is a multi-day running event taking place at the Sussex County Fairgrounds in Augusta, NJ, from October 2 to October 5, 2025. Participants can choose from various race formats, including 72-hour, 48-hour, 24-hour, 12-hour, and 6-hour races, as well as marathons and 50K ev..

The Run the Vineyards - Pindar Fall 8K is a scenic running event set in the picturesque Pindar Vineyards in Peconic, NY. Participants can choose between an 8K and a 5K race, both featuring flat courses primarily on hard-packed dirt trails and grass, making them walker-friendly. The event includes ch..

The KMT Fall Foliage Frenzy is a timed trail running event held in Montebello, NY, near Kakiat Park and Harriman State Park. Participants can choose between 3-hour and 6-hour race options, running on a challenging 2.33-mile loop with approximately 660 feet of vertical gain. The course offers stunnin..