Trail Running calendar near Windsor 2025-2026

The Sweltering Summer Ultra is an annual 8-hour running event held at Clapp Park in Pittsfield, Massachusetts. Participants can run or walk as many laps as they choose on a certified dirt and cinder track, with a total of 74 laps required for marathon completion. The event features a unique aid stat..

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 is a unique running event taking place in Chester, VT, featuring both 6-hour and 12-hour races on a scenic 1.8-mile loop with moderate elevation. This fun, community-oriented event encourages participants to bring food to share, fostering a collaborative atmosphere. Basic refreshments,..

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..

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 Macedonia Trail Race, hosted by Steep Endurance, takes place in Macedonia Brook State Park, Kent, CT, offering a unique trail running experience. Now in its 7th year, the event features stunning single-track trails, challenging climbs, and breathtaking viewpoints. Participants can choose from th..

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

Wilcox Wild is an exciting 50K ultra trail run set in the stunning Adirondack Park Wilderness, taking place on September 13, 2025. The race features a challenging course that begins and ends at Harrisburg Lake, traversing beautiful trails through the Wilcox Lake Wild Forest. Participants will encoun..

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 navigate a scenic loop course that combines pavement, grass, and single-track trails..

The Shawangunk Ridge Trail Run (SRT) is an exciting trail running event that showcases the stunning landscapes of the Shawangunk Mountains in New York. Participants can choose from three divisions: a 70-mile ultra, a 30-mile run, and a half marathon, catering to various skill levels. The event empha..

The Pisgah Mountain Trail Races, organized by the Red Clover Rovers, feature a 50K and a 23K trail race in Pisgah State Park, Chesterfield, New Hampshire. Scheduled for September 14, 2025, this event serves as a fundraiser for the New Hampshire Special Olympics, with all profits supporting their mis..

The Angevine Farm Trail Festival, hosted by Steep Endurance, is a family-friendly running event taking place in Warren, CT. Celebrating its 7th year, the festival features a variety of races including a Half Marathon, an 8-hour endurance challenge, and a 5K, with options for participants to run alon..

The Cat's Tail Trail Marathon is a challenging 26-mile trail race set in the scenic Slide Mountain Wilderness Area of the Catskill Mountains, New York. Scheduled for September 27, 2025, this rugged marathon features nearly 7,000 feet of elevation gain, offering participants breathtaking views and te..

The Vermont 50 Ultra Run is an annual event held in West Windsor, Vermont, featuring a variety of races including a 50-mile ultra run, a 50K run, and several mountain biking options. Established in 1993, the event supports Vermont Adaptive Ski and Sports, promoting confidence and independence for in..

The IronHike Endurance Series is a unique multi-day event taking place at Mohawk Mountain in Cornwall, CT, from October 2 to October 5, 2025. Participants can choose from various challenges, including individual and team formats, with distances ranging from 15 to over 152 miles, featuring significan..

The Flutters and Foliage Endurance Run is an annual fundraising event held in Cohoes, NY, organized by Flutters of Hope Inc., a nonprofit supporting individuals and families affected by eating disorders. This year marks its third edition, featuring various endurance challenges, including a 6-hour ru..

The NipMuck Trail Marathon is a challenging 26.4-mile race held on the scenic Nipmuck Trail in Ashford, Connecticut. Participants can choose between the full marathon or a relay option, where two runners share the distance. The course features a mix of terrain, including rocks, roots, and mud, makin..

The Groton Town Forest Trail Races, organized by the Squannacook River Runners and Groton Trails Committee, feature two scenic courses of 9.5 miles and 3.4 miles through the picturesque Groton Town Forest. The trails are well-marked and consist of narrow dirt roads and winding paths, presenting a mi..

The Midstate Massive Ultra Trail is an endurance running event taking place in New Ipswich, New Hampshire, featuring three challenging race options: 100-mile, 50-mile, and 30-mile courses. Set against the stunning backdrop of autumn in New England, the race follows the historic Midstate Trail, cross..

The Mohawk Mountain Race, organized by Steep Endurance, takes place at the Mohawk Mountain Ski Area in Cornwall, CT. This unique event transforms the ski mountain into a challenging running course featuring 5K, 10K, Half Marathon, and Marathon options. Participants will navigate steep ascents and de..