Trail Running calendar near Rocky Point 2025-2026

The Lake Mohegan Trail Race is a women's only trail running event held in Fairfield, CT, organized by Steep Endurance. Aimed at promoting trail running among women, the event typically sees 30-40% female participation, with over 125 runners in 2024. The race features three distance options: a 5K, a..

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 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..

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 is a unique trail running event held in Roosevelt Forest, Stratford, CT. Scheduled for May 3, 2025, this 9-hour ultra trail race invites participants of all levels, including runners, joggers, hikers, and walkers, to complete as many miles as they can on a well-marked..

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..

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 MCW Branch Brook Classic is a running event taking place at Branch Brook Park in Newark, NJ, featuring 3 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. Proceeds from the event support Missio..

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 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 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..

The Spring Fling 600 is an annual trail running event organized by the CT Trailmixers, taking place at YMCA Camp Sloper in Southington, CT. This year marks the eighth edition, featuring two race options: a 600-minute challenge where participants can run as many loops as they wish on a roughly three-..

The "Run Like A Mother" 5K Trail Run, organized by the Franklin Elementary School PTO, is a family-friendly event taking place at Giddings Park in North Franklin, CT. This Mother's Day-themed race celebrates the incredible role of mothers and is open to participants of all ages, including a special..

The SMR Mayapple Trail Runs, scheduled for May 17, 2025, in South Mountain Reservation, NJ, invites runners to participate in its 16th annual event. Organized by the South Mountain Conservancy, the race features various distances including 5 miles, 10 miles, 20 miles, 50K, and 50 miles, along with a..

The Run Ragged Last Person Standing event, hosted by the CT Trailmixers, is an exciting endurance race set in the rugged terrain of Ragged Mountain, Berlin, CT. Participants will tackle a challenging 3.11-mile loop, with one hour to complete each lap. The race continues until only one runner remains..

The MCW NJ Appalachian Trail Runventure is a unique running event scheduled for May 17, 2025, in Scotch Plains, NJ. Participants can choose between a marathon or a 40-mile run, both designed to provide a fully supported experience along the New Jersey Appalachian Trail. This event is also a fundrais..

The Nassau Suffolk Trail Marathon & 15 Miler is a premier running event taking place in Farmingdale, NY, on May 18, 2025. This event features two main races: a full marathon and a 15-mile trail run, both set in the scenic Bethpage State Park. Participants will enjoy a well-marked course that include..

The 16th Annual Farmington River Run 5K Trail Race is scheduled for May 18, 2025, at Winding Trails in Farmington, Connecticut. This scenic race takes place on a designated 5K trail within a 300-acre area surrounding Walton Pond. Participants can compete for awards in various categories, including o..