Trail Running calendar near Billings 2025-2026

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 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 running event taking place in Wawayanda State Park, NJ, featuring a variety of challenging trail distances including a 100K, 50 Mile, 50K, and Half Marathon. Participants will navigate through scenic routes filled with rhododendron tunnels, marsh bridges, and ..

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 features three race options: a 5K, a 10K, and a 4-hour challenge where participants can run or walk as many laps as possible ..

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..

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 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. Scheduled for May 4, 2025, the event aims to support The Hartsbrook School's unique programming, which includes land stewa..

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..