Trail Running calendar near Pittsfield 2025-2026

The F.I.T. Sun Mountain Challenge is an annual trail running event held at Bromley Mountain in Peru, Vermont. It offers three race distances: 5K, 10K, and a challenging 25K ultra.The course features beautiful mountain trails with gradual ascents and descents, including over 1,400 vertical feet per 3..

The Red Wing Trail Challenge, held at Red Wing Recreation Area in Lagrangeville, NY, offers two trail race distances: a challenging 60K with approximately 6,600 feet of elevation gain, and a 15K featuring about 1,650 feet of gain. The 60K consists of four laps of a 15K loop that includes varied terr..

The Undercliff/Overcliff race is the first event in the 52nd Summer Series hosted by Shawangunk Runners, held in Gardiner, New York. This iconic 4.7-mile loop race starts and finishes at Trapps Bridge, with parking available at the Mohonk Preserve West Trapps entry. Since 1974, the series has showca..

The 7-11 Slurpee Day Ultra 60k is a unique, self-supported ultramarathon held in Vernon, Connecticut, covering approximately 37.5 miles along mostly road routes. Participants run between seven 7-11 convenience stores across towns including Vernon, Manchester, East Hartford, West Hartford, Newington,..

The Notchview Ultra is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with aid sta..

The Rails-to-Trails 5K in East Hampton, Connecticut, is a point-to-point race starting at the Connecticut Draft Horse Rescue and finishing at the Old Home Days grounds. The scenic course begins on Chestnut Hill Road, crosses Route 16, and continues along the shaded Air Line Trail for about two miles..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. It features a challenging 7-mile course through scenic forest trails, offering runners a chance to experience natural beauty and varied terrain. The race is part of the USATF Connecticut Mountain..

The Landis Arboretum 5K Forest Run, held in Esperance, NY, is a scenic cross-country race through the arboretum’s forests and meadows, offering beautiful views of the Schoharie Valley. This rolling 5K course is part of the Route 20 Challenge Series and is USATF sanctioned. The event features chip ti..

The Slate Valley Scramble, organized by Slate Valley Trails, is a trail running event taking place on August 9, 2025. Participants can choose between an 8k and a half marathon, both set on scenic singletrack and double-track trails in Vermont's Slate Valley. A Kid's Fun Run is also available for chi..

Lover's Lane in Chester, Vermont, is a unique 6- or 12-hour running event featuring a 1.8-mile loop course with 280 feet of elevation gain and loss per lap. The trail combines single and double-track paths along with jeep trails, offering a moderately challenging terrain. The race starts and finishe..

The Sweltering Summer Ultra is an annual running event held at Clapp Park in Pittsfield, Massachusetts. The 13th edition features an 8-hour race on a certified 0.355-mile dirt and cinder track, with runners switching directions halfway through. Participants can run or walk as many laps as they choos..

Climb It For Climate is a mountain trail running event held at Belleayre Mountain Ski Center in the Catskill Mountains, New York. Participants can choose between a challenging 25K course, approximately 15 miles with 5,000 feet of elevation gain and descent, or a shorter 8K course of about 5 miles wi..

The Tappen Brook 5K, held in Bridgewater, Connecticut, is an annual trail running event hosted by the Bridgewater Land Trust and the Bridgewater Recreation Commission. Set in the scenic Bridgewater Town Park, the course features newly developed trails winding through forested woodlands with gentle h..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Jug End Loop Ultra is a 6-hour ultra running event held at Jug End State Reservation in Egremont, Massachusetts. Participants run multiple laps of a scenic 4.2-mile course featuring woods, fields, and an apple orchard, with an elevation change of 830 feet per lap. The course includes uphill and..

The Thacher Park Trail Running Festival, established in 2014, takes place at Thacher State Park in Voorheesville, NY. This scenic event offers participants a choice of four race distances: 10K, 13.1M, 26.2M, and 50K, allowing runners to experience the park's beautiful trails. The festival promotes a..

The Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course is a beautiful loop featuring gently rolling terrain on a mix of grassy trails, dirt roads, and single track, primarily on the west side of the Black River and North Sp..

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, traversing the state north to south along the scenic and flat Farmington Canal Heritage Trail. Starting in West Suffield and ending at New Haven Harbor, the course passes throu..

The Wicked Mudder will take place in Southwick on Sunday 7 September 2025. You can run between 5 and 5 kilometers.