Trail Running calendar near Great Barrington 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 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 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 with approximately 15 miles and 5,000 feet of elevation gain and descent, or a shorter 8K course covering about 5..

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 Fabulous Fahnestock Trail Races take place in Fahnestock State Park, Cold Spring, NY, offering distances of 50K, 25K, and a 5.5-mile race. The course features a mix of runnable dirt roads and technical single-track trails, with scenic views including lakes, ponds, and old rail beds. Runners expe..

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..

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 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..

Raptor Ridge, presented by Peace, Love, Trails, is a challenging 6.5-mile trail race held at the Westmoreland Sanctuary in Mount Kisco, New York. The course winds through the Sanctuary's 669-acre nature preserve, which features 8.5 miles of hiking trails across Bedford, Mount Kisco, and Armonk. The..

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.

The Macedonia Trail Race, held annually in Macedonia Brook State Park in Kent, Connecticut, offers trail runners a unique and challenging experience with its lush forest trails, technical singletrack, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on..

The Pawling 24 Hour Trail Running Festival, held in Pawling, NY at Lakeside Park, offers runners a challenging and festive endurance experience. Participants can choose from 3, 6, 12 (including a night start), or 24-hour timed races on a 1.68-mile loop course featuring pavement, grass, and single-tr..

The Storybook Half Marathon is a scenic 13.1-mile trail race held in Roosevelt Forest, Stratford, Connecticut. The course consists of eight loops on a 1.64-mile wooded trail featuring singletrack and doubletrack paths with roots, rocks, and gentle hills, offering a charming yet moderately challengin..

The Mountain Goat Cabin Trail Run takes place at the Merck Forest and Farmland Center in Rupert, Vermont. The main event features a challenging 7-mile loop with approximately 1,500 feet of elevation gain, winding through scenic trails and forest roads. Runners experience two historic cabins, Ned's P..

The PCS Harvest Hustle 5K & Kids Run is a community-focused event held at Pomfret Rec Park in Pomfret Center, Connecticut. It features a 5K trail run and a kids' fun run of half a mile, supporting the Pomfret Community School Parent Teacher Organization. The PTO uses funds raised to enhance educatio..