Trail Running calendar near Fairfield 2025-2026

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, New York. The event is known for its scenic course and community spirit, attracting participants of all ages, from 7 to 107. Due to its popularity, entry is determined through a lottery system.The registration fee includes t..

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..

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 Bear Mountain Trail Challenge will take place in Bear Mountain on Saturday 3 May 2025. You can run between 10 and 50 kilometers.

The VCP50k is an ultramarathon event taking place in Van Cortlandt Park, Bronx, NY. Established in 2023, this race is designed to be accessible for novice runners while still providing a challenge for experienced participants. The course consists of ten loops of a classic cross-country track, featur..

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, the course consists of a flat 2-mile loop made of soft regenerative rubber, ideal for both competitive runners and c..

The Blue 2 Blue Challenge is a demanding 50K trail race set in New Haven, Connecticut, known for its challenging terrain and technical trails. Scheduled for May 4, 2025, this event features a rigorous out-and-back course that includes significant elevation gain and rocky paths, making it suitable fo..

The Breakneck Point Trail Runs, organized by Red Newt Racing, is a challenging trail running event set to take place on May 4, 2025, in Beacon, NY. Participants can choose between a half marathon (13.1 miles) and a full marathon (26.4 miles), both featuring significant elevation gains and technical ..

The Ansonia Trails 5K is a running event taking place in Ansonia, CT, designed for participants of the 169 Society. This second annual race features a unique course consisting of two laps around a 1.55-mile loop, making it slightly over or under a traditional 5K distance. Limited to 50 runners, the ..

The "3 Days at the Fair" event in Augusta, NJ, scheduled for May 12-18, 2025, offers a variety of ultra-running challenges, including 144-hour, 72-hour, 48-hour, 24-hour, 12-hour, and 6-hour races, as well as marathon and 50K options. The course features a certified 1-mile loop composed of pavement ..

The Macho Trail Run is an exciting running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for May 17, 2025, the event features two main races: a 5-mile Adult Trail Run for participants aged 19 and older, and a 5-mile High School or Youth Trail Run for those aged 18 and und..

The SMR Mayapple Trail Runs, taking place on May 17, 2025, in South Mountain Reservation, NJ, offers a variety of trail races including 50 miles, 50K, 20 miles, 10 miles, 5 miles, and a Kids 1-Mile Run. Organized by the South Mountain Conservancy and supported by local volunteers, the event features..

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 of which are fully supported with shuttling, aid stations, and experienced pacers. This event serves as a fundraising ..

C'mon Armageddon is an exhilarating running event set in the challenging terrain of Norvin Green State Park, West Milford, NJ. Scheduled for May 18, 2025, participants can choose from three race distances: a grueling 50K with over 7000 feet of elevation gain, a 10 Miler with 2000 feet, or a 5 Miler ..

The Spring Run The Farm event, scheduled for May 18, 2025, in Katonah, NY, features a 5-mile trail race and two kids' races. The main event is open to participants aged 6 and older, while the kids' races cater to ages 7-12 and 6 and under. The race takes place at Muscoot Farm, showcasing the park's ..

The Soapstone Mountain Trail Races, taking place on May 18, 2025, in Stafford Springs, CT, feature two scenic races: a 25K and a 6K "Sampler." Both courses wind through the picturesque Soapstone Mountain area and Shenipsit Forest State Park, offering a mix of challenging terrain and beautiful views...

The Mine Hill Half Marathon, hosted by Steep Endurance, is touted as one of the toughest road half marathons in Connecticut. Set against the picturesque backdrop of the Mine Hill Distillery in Roxbury, participants will enjoy stunning views of farms, fields, and scenic vistas throughout the race. Th..

The Forest Park Runners Classic 4 Mile Road and Trail Race is an exciting running event scheduled for May 25, 2025, in Woodhaven, NY. Participants will enjoy a scenic 4-mile out-and-back course that traverses the beautiful trails and roads of Forest Park, starting and finishing at Victory Field Trac..