Trail Running calendar near Garrison 2025-2026

The John Jay Community Trail Race is a competitive running event taking place in Cross River, NY, featuring a 5k race, a 4k Jay Walk, and a Kids Jay Dash. The 5k course winds through the scenic John Jay Community Cross Country Trail, offering challenging and hilly terrain. The 4k Jay Walk is a non-c..

The Spring SOMO Timed Trail Races is a running event scheduled for April 12, 2025, at South Mountain Reservation in South Orange, NJ. Participants can choose from various race formats, including a 3K loop, 6K loop, and timed events lasting 1, 3, or 6 hours. The course features a mix of single track,..

The Brookhaven Trail 15K and 4 Mile Trail Run is set to take place at Brookhaven State Park in Wading River, NY. This popular event features a challenging course that includes various trail conditions, from single-track paths to sandy sections, all within the scenic woodlands of Suffolk County. Part..

The Traprock 50 is a challenging trail running event held at Penwood State Park in Bloomfield, CT, featuring two race distances: a 50K and a 17K. The course consists of approximately 10.5-11 miles per loop, with the 50K requiring three loops and the 17K one loop. Runners will navigate a mix of techn..

Shore2Shore is an exciting running event taking place in East Islip, NY, featuring a scenic 50K and 25K race along the beautiful Suffolk County Long Island Greenbelt Trail. Participants will experience a point-to-point course that starts at Sunken Meadow and finishes at Heckscher State Park, with fu..

The 47th Annual Woods and Lakes Run is set to take place in Mountain Lakes, New Jersey, featuring both a 10K and a 5K race. Open to participants aged 30 and over, the event promises a scenic course that includes a mix of macadam walkways, gravel paths, and wooded trails, with potential challenges su..

The Sterling Squatch Half Marathon, part of the Squatchywaska Mountainfest, offers participants a challenging and scenic experience through the stunning trails of the Shawangunk Ridge. With two course options—25K and 10 miles—runners will navigate rugged terrain, steep climbs, and breathtaking views..

The Wawayanda Trail Fest is an exciting endurance event taking place in Vernon Township, NJ, featuring a variety of race distances including a 100K, 50 Mile, 50K, and Half Marathon. Set against a scenic backdrop of rhododendron tunnels, marsh bridges, and diverse terrain, the course offers a challen..

The Lake Mohegan Trail Race is a women's only trail running event held in Fairfield, CT, aimed at promoting trail running among women. Scheduled for April 26, 2025, the race features three distances: a 5K, a 10K, and a 4-hour option for participants to run or walk as many laps as possible on a 5K lo..

Squatchywaska Mountainfest is an exciting trail running event taking place in Ellenville, NY, featuring two challenging courses: a 25K and a 10-mile race. Participants will navigate stunning mountain singletracks, experiencing breathtaking views of the Catskills and the iconic Verkeerder Kill Falls...

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Kent, Connecticut, marking its 51st anniversary. Known as the oldest 100K race in the United States, it features three race distances: 100K, 50 miles, and 50K, all set on scenic, primar..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages. The event emphasizes community and outdoor activity, taking place in a scenic park setting. Due to its popularity, entry is determined through a lottery system.The registration fee in..

The Forgotten Forest Ultra Run, taking place in Stratford, CT, is a unique 9-hour trail running event set in the scenic Roosevelt Forest. Participants can choose to run, jog, hike, or walk on a well-marked loop trail featuring an elevation gain of approximately 131 feet per loop. This friendly compe..

The Bear Mountain Trail Challenge is an exciting running event set in Bear Mountain State Park, located just an hour from New York City. Participants can choose from three race distances: a 50K, a half marathon (21K), and a 10K. The course features a diverse range of terrains, including short climbs..

The Trails To the Sky 50k/10k is an exciting trail running event scheduled for May 3, 2025, at Voorhees State Park in Glen Gardner, NJ. Participants can choose between a 50k or a 10k course, featuring scenic trails with significant elevation gains of approximately 4500ft for the 50k and 900ft for th..

XTERRA New Jersey is an exciting off-road sports event taking place in Wawayanda State Park, New Jersey. Scheduled for May 3-4, 2025, it is part of the XTERRA World Tour and features a variety of races, including off-road triathlons, duathlons, and trail runs. Participants can choose from multiple d..

The VCP50k is an ultramarathon event taking place in Van Cortlandt Park, Bronx, NY, designed to cater to both novice and experienced runners. Established in 2023, the race features a challenging course consisting of ten loops of a classic cross-country track, with an overall elevation gain of approx..

The MCW Branch Brook Classic is a running event taking place at Branch Brook Park in Newark, NJ, featuring 3-hour and 6-hour races. Set against the backdrop of the Cherry Blossom Festival, participants will navigate a flat 2-mile loop designed for speed and comfort. The event aims to raise funds for..

Frosty Woods - a Winter Way over Yonder Trail Adventure is part of the 2023 Trail Run Series organized by Ready Set Go Adventures. This event features a variety of race distances, including a marathon, half marathon, 10K, and 5K, catering to runners of all skill levels. Participants can compete for..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Participants will navigate some of the toughest trails in the state, including the Regicides and Quinnipiac Trails, with a total elevation gain of approximat..