Trail Running calendar near Chesterfield 2025-2026

The People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. Celebrating its 26th edition in 2025, the race is part of the USATF Connecticut Mountain Ultra Trail (MUT) series championship. The course starts and finishes near the Matheis Grove Pavilion on Ea..

The Pete Hawley People's 7 is an annual 7-mile trail running event held in Barkhamsted, Connecticut, at the Matheis Grove Pavilion on East River Road. This USATF-sanctioned race features a scenic course starting on the Blue trail, transitioning to Yellow and Orange trails before returning to Blue fo..

The Churney Gurney 5 Mile Trail Race is an annual event held in Queensbury, NY, featuring a challenging 5-mile trail run on the scenic Gurney Lane Trails. The course includes lots of single track paths with various ups and downs, offering a great trail running experience. The race starts and finishe..

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..

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..

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 Shenipsit Striders 50th Fatass is a celebratory running event held at Crandall's Park Pavilion in Tolland, Connecticut. Marking the club's 50th anniversary, the event features an 8-hour window where participants run multiple 5K loops on a trail course starting and finishing at the pavilion. Runn..

The Midstate Massive Course Preview is a pre-race recon run held in Spencer, Massachusetts, offering runners a chance to explore a 13.1-mile section of the Midstate Trail used in both the 50-mile and 100-mile races. The run covers the trail segment between Aid Stations 6 and 8, providing participant..

The GTA Challenge is a 10K trail race held in Greenfield, New Hampshire, organized by the Greenfield Trail Association to support local trail maintenance. The course features a mix of class 6 roads, double track, and single track trails with natural obstacles like rocks and roots, offering a challen..

Serenity on the Trails is a 4-mile trail race held in Schenectady Central Park, New York. The event features an open time trial format, allowing runners to start their timed lap anytime between 8 and 11 AM, with the course closing at noon. The race honors the memory of Ellen Wisnoski and supports Se..

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 Saratoga Community & Cross Country 5K Challenge is a running and walking event held at Pitney Meadows Community Farm in Saratoga Springs, NY. The event features a 5K Run/Walk and a free 5K Run/Walk for kids aged five and under. Participants can enjoy a lively atmosphere with music, a food truck,..

The Thacher Park Trail Running Festival, held annually at Thacher State Park in Voorheesville, NY, offers a scenic and challenging trail running experience. Participants can choose from four distances: 10K, half marathon (13.1 miles), marathon (26.2 miles), and an ultra 50K. The course features a sh..

The Triple Dam 10K is a scenic running and walking event held at the Power Dam Recreation Area in Perkinsville, Vermont. The course features a beautiful loop on gently rolling terrain, combining grassy trails, dirt roads, and single track paths along the Black River and North Springfield Reservoir...

The Old Goat Track Club XC Classic is a 5K cross-country race held at Water's Farm in Sutton, Massachusetts. Scheduled for August 24, 2025, it features separate Women's and Men's Open 5K races. The event serves as the first race in the USATF New England XC Grand Prix series and is part of the USATF..

The Springfield Dam Run, held in Springfield, Vermont, offers a family-friendly running event featuring three races: a Kids 1/2 Mile Fun Run for children 12 and under, a new Maniac Mile one-mile sprint for ages 10 and up, and the traditional 3.1-mile Springfield Dam Run. The main race takes place on..

The TARC Fall Classic is a popular trail running event held at Great Brook Farm State Park in Carlisle, Massachusetts, offering a range of distances including 10K, half marathon, 20 mile, 50K, and 50 mile races, plus a Yeti Mischief Mile and a free youth fun run. The courses wind through scenic New..

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.