Trail Running calendar near Roxbury 2025-2026

The Angevine Farm Trail Festival, hosted by Steep Endurance, takes place in Warren, Connecticut, showcasing the region's scenic trails and beautiful fall foliage. This annual event features a variety of races, including a Half Marathon, 5K, and a unique 8-hour challenge, all set against a backdrop o..

The Water Gap 50k and Half is a scenic trail running event set in the picturesque Delaware Water Gap, Pennsylvania. Participants can choose between a 50K or 25K distance, both of which traverse the beautiful McDade Trail, known for its mix of cinder paths and singletrack terrain. The event celebrate..

The Cat's Tail Trail Marathon is an exciting point-to-point trail marathon set in the stunning Slide Mountain Wilderness Area of the Catskill Mountains, New York. Scheduled for September 27, 2025, this challenging race features nearly 7000 feet of elevation gain, offering participants breathtaking v..

The IronHike Endurance Series, taking place at Mohawk Mountain in Cornwall, CT, is a unique multi-day event designed for both individual participants and teams. Scheduled for October 2-5, 2025, it features various challenges, including the Kuwohi, Double K, Denali, Everest, and Olympus Mons Ultra, e..

The Mohawk Mountain Race, organized by Steep Endurance, takes place at the Mohawk Mountain Ski Area in Cornwall, CT. This unique event transforms the ski mountain into a challenging running course featuring 5K, 10K, Half Marathon, and Marathon options. Participants will navigate steep ascents and de..

Big Bear Squatchtoberfest is a trail running event hosted by Sassquad Trail Running in collaboration with the New York-New Jersey Trail Conference. Set in Harriman State Park, Tuxedo, New York, this event features a challenging half marathon and a 10K race, showcasing the park's rugged terrain and s..

The Fall Back Into The Trails Series is an annual running event hosted by C.T.W Endurance, taking place at the Red Wing Recreation Area in Lagrangeville, NY. Scheduled for November 1-2, 2025, the series features three race options: a challenging 100k, a 50k with five loops, and a 10k. Participants c..

The Saratoga Stryders Fall Back 5 Mile Trail Race is an exciting running event held at Saratoga Spa State Park. Participants can enjoy a scenic course featuring hills, ridges, and a mix of trails, showcasing the park's natural beauty. The race encourages runners to embrace the autumn season, with re..

Rob's Trail Run Edition is a running event taking place at Stillwell Woods Preserve in Woodbury, NY. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run and a 5K High School or Youth Trail Run, catering to participants of different age groups. This event aims to ..