Trail Running calendar near Windsor 2025-2026

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..

The Serenity on the Trails will take place in Schenectady on Saturday 16 August 2025. You can run 4 miles.

The New Paltz Pizza Challenge is a fun and unique 3.3-mile running event held in New Paltz, NY, starting at Water Street Market. The course is approximately 5 kilometers and offers participants a lively atmosphere with plenty of pizza to enjoy along the way. The event features prizes for the winners..

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 a challenging elevation change of 830 feet per lap. The course includes..

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 will take place in Springfield on Saturday 6 September 2025. You can run 3 miles.

The Cross-Connecticut Run for Mental Health Awareness is a unique 56-mile group running event held annually in Connecticut, following the scenic and flat Farmington Canal Heritage Trail from West Suffield to New Haven. This non-competitive challenge supports Mental Health Connecticut through fundrai..

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 in Macedonia Brook State Park in Kent, Connecticut, offers a unique trail running experience with lush singletrack trails, challenging climbs and descents, and stunning viewpoints including Cobble Mountain, where runners can see the Catskill Mountains on clear days. No..

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..

Wilcox Wild is a challenging 50K trail ultra run held in the Adirondack Park Wilderness, New York, on September 13, 2025. The race features a rugged lollipop course starting and finishing at Harrisburg Lake, covering 31 miles with 3,028 feet of elevation gain and loss. Runners traverse scenic trails..

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 Lucy Mac 5K9 is a trail running event held at Ascutney Outdoors in Brownsville, Vermont. Scheduled for September 13, 2025, it features a timed 5K race and a 1-mile race option, welcoming runners, walkers, and dogs. The course offers a scenic Vermont adventure with handcrafted trails at the weste..

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..