Trail Running calendar near Ashford 2025-2026

The Spring Fling 600 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. The event features two main races: the 600-minute race where participants run as many loops as possible on a roughly three-mile trail course within 10 hours, and a 6-mi..

The Watuppa Trail Races is an annual running event held in Fall River, Massachusetts, celebrating its 11th year in 2025. Participants can choose from three race distances: 10K, 30K, and 50K, catering to various skill levels and preferences. The event takes place in the scenic Watuppa Reservation, pr..

The TARC Wapack and Back is a challenging trail running event organized by the Trail Animals Running Club, taking place along the scenic Wapack Trail in Ashburnham, Massachusetts. Participants can choose from three distances: 21.5 miles, 43 miles, and 50 miles, with the course featuring rocky ledges..

The "Run Like A Mother" 5K Trail Run, organized by the Franklin Elementary School PTO, is a family-friendly event taking place at Giddings Park in North Franklin, CT. This Mother's Day-themed race celebrates the incredible role of mothers and is open to participants of all ages, including a special..

The Tails & Trails State Forest Run, scheduled for May 17, 2025, in Pittsfield, MA, features three race distances: 50K, 25K, and a 5 Miler. This event supports local animal rescue nonprofits, including Red Robin Song Animal Sanctuary, No Paws Left Behind, and Berkshire Bird Paradise, Inc. Participan..

The Dash For Dane & Family Day is an annual event held at Powisset Farm in Dover, MA, designed to honor the memory of Dane and support important causes. The event features a 5K Trail Run/Walk, a 1K Kids Fun Run/Walk, and various family-friendly activities such as magic shows, crafts, and live music...

The Run Ragged Last Person Standing event, hosted by the CT Trailmixers, is an exciting endurance race set in the rugged terrain of Ragged Mountain, Berlin, CT. Participants will tackle a challenging 3.11-mile loop, with one hour to complete each lap. The race continues until only one runner remains..

The Free Spirit 50k is a scenic ultramarathon held in Leyden, Massachusetts, featuring a challenging dirt road course with 4,200 feet of elevation change. Runners experience beautiful New England landscapes, including forests, fields, and a historic 1870s covered bridge. The event starts and finishe..

The 16th Annual Farmington River Run 5K Trail Race is scheduled for May 18, 2025, at Winding Trails in Farmington, Connecticut. This scenic race takes place on a designated 5K trail within a 300-acre area surrounding Walton Pond. Participants can compete for awards in various categories, including o..

The Soapstone Mountain Trail Races, held in Stafford Springs, Connecticut, offer two scenic trail running events: a challenging 25K (approximately 15.5 miles) and the Jerry Stage 6K "Sampler." Both courses wind through the beautiful Soapstone Mountain area within Shenipsit Forest State Park, featuri..

The 4K Trail Run is a unique running event taking place in Boston, featuring individual and corporate team registrations. Scheduled for May 21 and 22, 2025, participants can join as individual runners or as part of a corporate team. The event aims to support Boston's youth through fundraising effort..

The Flints Pond Trail Run is a new event aimed at raising funds for the Birches School while offering a scenic and challenging course on the Lincoln Land Trust Trails at Flint's Pond. The run takes place in a beautiful natural setting, providing participants with an enjoyable outdoor experience. Ame..

The Womp Romp Women’s Group Run is a welcoming running event held at Wompatuck State Park in Hingham, Massachusetts. Participants can choose to run distances ranging from 5 to 10 miles or more, accommodating various paces and preferences. The park offers a scenic and historic setting, featuring exte..

The Taunton Trail Half Marathon is an exciting running event designed for both beginners and experienced trail runners. Set in the picturesque surroundings of Taunton's waterways, the course is ultra-flat and fast, making it ideal for those looking to achieve personal bests. Participants can look fo..

The Mine Hill Half Marathon, held in Roxbury, Connecticut, is known as the toughest road half marathon in the state. Starting and finishing at the scenic Mine Hill Distillery, the challenging 13.1-mile course features a mix of paved and dirt roads with significant elevation changes, including a stee..

The Powisset Farm Trail Run - Spring is a part of the Barn to Run Trail Race Series, taking place on Memorial Day, May 26, 2025, at Powisset Farm in Dover, MA. Participants can choose from four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, all set against the scenic backdrop of Pow..

The Chesterfield Gorge Ultra & 25k is a unique running event held at the Chesterfield Gorge Reservation, featuring a 'choose your own adventure' format. Participants can select from various distances, including 100 miles, 100k, 50 miles, 50k, and 25k, with staggered starts to manage the flow of runn..

The Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run is a 5-mile running event taking place along the scenic Cheshire Rail Trail, starting from the original Fitzwilliam Railroad Depot to the newly restored Troy Depot. This event celebrates the historical significance of the rail trail, whic..

The IronHike Endurance Series - Spring 2025 takes place at Mohawk Mountain Ski Area in Cornwall, Connecticut. This multi-day event, held over four days in June, offers a unique blend of hiking, trail running, and camping challenges. Participants can compete solo, with a trail buddy, or as a trail fa..

The Flanders Field & Forest 5K is an annual trail run and walk held at Flanders’ Van Vleck Farm & Nature Sanctuary in Woodbury. Covering 3.1 miles of scenic trails, the event welcomes participants of all ages and fitness levels. It is officially timed and features divisions for different age groups,..