Trail Running calendar near Woodbury 2025-2026

The Lake Mohegan Trail Race is a women’s-only trail running event held in Fairfield, Connecticut, organized by Steep Endurance. Scheduled for April 26, 2025, it features three race options: 5K, 10K, and a 4-hour run/walk challenge on a scenic, well-maintained trail loop. The event aims to promote tr..

The Wawayanda Trail Fest is a challenging trail running event held in Vernon Township, New Jersey, at Wawayanda State Park. Scheduled for April 26, 2025, it features multiple race distances, including a 100K, 50 Mile, 50K, and Half Marathon, with courses winding through scenic hills, lakes, and dens..

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..

Squatchywaska Mountainfest is a challenging trail running event held in Ellenville, NY, featuring 25K and 10-mile courses through the scenic Shawangunk Ridge. Runners will navigate rugged, technical singletracks, steep climbs, and breathtaking vistas, including views of the Catskills and Verkeerder..

The Jack Bristol Lake Waramaug Ultra Races, taking place on April 27, 2025, is a celebrated ultra-running event in Connecticut, marking its 51st anniversary. This historic race features three distances: 100K, 50 miles, and 50K, all set around the scenic Lake Waramaug. Participants can expect well-st..

"Your Story Matters" is a Falcon 5K Run/Walk event aimed at raising mental health awareness, taking place at Jefferson Township High School in Oak Ridge, NJ. The event features a Youth Color Run for children, encouraging them to participate in a fun and colorful experience, and a 5K Trail Run for pa..

Leatherman's Loop is a popular 10k trail race held annually in Cross River, NY, attracting participants of all ages from 7 to 107. The event is known for its scenic course and community spirit, and entry is determined through a lottery system due to high demand. The registration fee includes the par..

The Conquer The Trail 5k is an annual running event celebrating its 10th year, taking place at Mercy University in Dobbs Ferry, NY. This year, the race will feature a flat and fast out-and-back course along the Old Croton Aqueduct Trail, with a single hill before the finish. Proceeds from the event..

The Forgotten Forest Ultra Run in Stratford, CT, is a 9-hour trail endurance event held in Roosevelt Forest. Participants can run, hike, or walk on a well-marked 2.2-mile loop with approximately 131 feet of elevation gain. The race is designed for runners of all levels, whether aiming for a personal..

The 47th Annual Woods and Lakes Run is a running event taking place in Mountain Lakes, New Jersey. This event features two races: a traditional 10K and a simultaneous 5K, both open to participants aged 30 and over. The scenic course includes a mix of macadam walkways, gravel paths, and wooded trails..

XTERRA New Jersey is an outdoor endurance event held in Wawayanda State Park, featuring a variety of races including off-road triathlon, trail runs, mountain biking, gravel biking, and duathlons. The event takes place over two days in early May 2025 and offers participants scenic courses through the..

The VCP 50K 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 appro..

The Frosty Woods - a Winter Way over Yonder Trail Adventure will take place in Ringwood from Saturday 3 May 2025 to Sunday 4 May 2025.

The 7 Sisters Trail Race is an exciting running event that features a series of wave starts based on anticipated finish times, ensuring a well-organized experience for participants. Runners are required to carry their own water, as the race is cupless, promoting sustainability. The event is capped a..

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..

A Run to Remember is a community-focused running event taking place at The Farm Trails at Greig Farm in Red Hook, NY. Scheduled for May 3, 2025, the event features a 5K Trail Run and a 5K Walk, designed to honor loved ones who have passed away while promoting health and togetherness. Participants ca..

The MCW Branch Brook Classic is a running event held in Newark, NJ, at Branch Brook Park, coinciding with the Cherry Blossom Festival. Participants can choose between a 3-hour or 6-hour race on a flat, 2-mile loop course made of soft regenerative rubber, ideal for fast running or impact reduction. T..

The Dandelion Dash and Mushroom Mile is a fun running event taking place in Hadley, MA, featuring a 5K trail run or walk and a 1-mile race suitable for participants of all ages. This event aims to support The Hartsbrook School's unique programming, which includes land stewardship and sustainable pra..

The Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail race held in Beacon, NY, on May 4, 2025. The event features a half marathon (~14.5 miles, 4,800’ gain) and a full marathon (~26.4 miles, 9,000’ gain), both offering technical terrain, steep climbs, and breathtaking..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. This event, which runs along the Regicides and Quinnipiac Trails, features over 6,350 feet of elevation gain, making it one of the toughest races in the stat..