Trail Running calendar near Pittsfield 2024-2025

We have found 39 Trailruns within 80 miles of Pittsfield. See below where and when you can find the races.

The Ansonia Six Hour Trail Run is an exciting endurance event taking place at the Ansonia Nature Center in Ansonia, Connecticut. Participants will tackle approximately 1.9-mile loops on moderately technical singletrack trails, featuring about 170 feet of elevation gain per loop. Scheduled for the se..

Manitou’s Revenge is a challenging 53-mile ultramarathon set in the scenic Catskill Mountains, starting in Windham, NY. The course features approximately 15,000 feet of elevation gain, with rocky and steep terrain that requires runners to be prepared for both hiking and technical sections. Participa..

The Free to Run Trail Races, organized by the Berkshire Ultra Running Community for Service (BURCS), will take place on June 21, 2025, in Pittsfield State Forest, Massachusetts. This event features three race distances: 15K, 25K, and 50K, designed to challenge participants with scenic trails, signif..

The Brooksvale 12-Hour event is a unique running challenge set in Hamden, CT, featuring a 4.25-mile loop course with a total elevation gain of 500 feet per loop. Participants can aim for various distances, including a marathon, 50k, or even 50 miles, making it suitable for runners of all levels. The..

July 2025

The F.I.T. Sun Mountain Challenge is an exciting running event taking place at Bromley Mountain in Peru, Vermont. Scheduled for July 5, 2025, the challenge features three race options: a 5K, 10K, and a 25K ultra, catering to participants of all skill levels.Runners will enjoy stunning mountain views..

The Notchview Ultra is an exciting multi-day running event scheduled for July 11-14, 2025, in Windsor, MA. Participants can choose from various race formats, including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours, all set on a scenic 1.9-mile loop trail. The event features well-s..

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place in Vernon, CT, on July 11, 2025. Participants will cover a self-supported distance of 37.5 miles, stopping at various 7-11 locations along the route. The event encourages a fun and relaxed atmosphere, with no strict course or pace..

August 2025

The 2025 Landis Arboretum 5K Forest Run is set to take place in Esperance, NY, featuring a scenic cross-country course through the Arboretum's forests and meadows, offering stunning views of the Schoharie Valley. This event, now in its 19th year, includes runner awards in ten-year age groups, team c..

The Sweltering Summer Ultra is an annual running event taking place in Pittsfield, Massachusetts, featuring an 8-hour race on a certified dirt and cinder track. Participants can run or walk as many laps as they choose, with a total of 74 laps required to complete a marathon distance. The event inclu..

Climb It For Climate is an exciting mountain running event set in the picturesque Catskill Mountains at Belleayre Resort. Participants can choose between a challenging 25K or a shorter 8K course, both offering stunning views and a chance to enjoy the great outdoors. This event emphasizes sustainabil..

The Jug End Loop Ultra is an exciting running event scheduled for August 23, 2025, at Jug End State Reservation in Egremont, MA. Participants can engage in a 6-hour ultra event, completing as many laps as possible on a scenic 4.2-mile course that features a mix of woods, fields, and an apple orchard..

September 2025

The Pawling 24 Hour Trail Running Festival is an exciting endurance event taking place in Pawling, NY, featuring a variety of race options including 24-hour, 12-hour, 6-hour, and 3-hour challenges. Participants will run on a scenic 1.68-mile loop that combines pavement, grass, and single-track trail..

The Shawangunk Ridge Trail Run (SRT) is a scenic running event taking place in the Shawangunk Mountains, New York, featuring three divisions: a 70-mile ultra, a 30-mile run, and a half marathon. The trail showcases diverse landscapes, including rolling hills, wetlands, and stunning views across five..

The Gardiner Dump Run is an exciting running event scheduled for September 21, 2025, in Gardiner, NY. Participants can choose between a 5k trail run or a 10k option, which consists of two laps of the 5k course. The race takes place on scenic single-track trails through wooded hillsides near the Wall..

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..

October 2025

The IronHike Endurance Series, taking place at Mohawk Mountain in Cornwall, CT, is a unique multi-day event designed for hiking and trail running enthusiasts. Scheduled for October 2-5, 2025, participants can choose from various challenges, including individual and team formats, with distances rangi..

The Midstate Massive Ultra Trail is an endurance running event taking place in New Ipswich, New Hampshire, featuring three challenging race options: 100 miles, 50 miles, and 30 miles. Set against the stunning backdrop of New England's autumn, the course traverses the Appalachian Midstate Trail, cros..

The Mt. Tom Trail Race, organized by Beast Coast Trail Running, offers participants a chance to explore the scenic beauty of Mt. Tom during peak foliage.The event features challenging courses, including a solo 25k, a 2-person relay, and a solo 10k, all set within the rugged terrain of Mt. Tom State ..

November 2025

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..