Trail Running calendar near Upton 2025-2026

The 7-11 Slurpee Day Ultra 60k is a unique self-supported ultramarathon held in Vernon, Connecticut, covering approximately 37.5 miles on mostly road routes. Participants run between multiple 7-11 convenience stores across towns including Vernon, Manchester, East Hartford, West Hartford, Newington,..

The Notchview Ultra is a multi-day ultrarunning event held in Windsor, Massachusetts, featuring a variety of race durations including 100.7 miles, 72 hours, 48 hours, 24 hours, 12 hours, and 6 hours. The course is a scenic, well-maintained 1.9-mile perimeter loop trail around Notchview, with aid sta..

The Rails-to-Trails 5K in East Hampton, Connecticut, is a point-to-point race starting at the Connecticut Draft Horse Rescue and finishing at the Old Home Days grounds. The scenic course begins on Chestnut Hill Road, crosses Route 16, and continues along the shaded Air Line Trail for about two miles..

The 12 Hours of Lawrence Woods is a half-day ultrarunning event held in Medford, Massachusetts, within the scenic Lawrence Woods section of the Middlesex Fells Reservation. Participants run a roughly 5-mile loop course that stays within the woods without crossing over itself, sharing only one inters..

Ocean State Ultra is an endurance running event held at Big River State Management Area in West Greenwich, Rhode Island. The race offers three categories: a 100-mile ultra, a 12-hour, and a 6-hour race, all conducted on a 10-mile loop course featuring 1.5 miles of desert, 1 mile of pavement, and 7.5..

The Soapstone Assault is a challenging approximately 5-mile trail race held at Soapstone Mountain, featuring a unique course that requires participants to climb the mountain six times. This event is designed for those seeking a rigorous hill workout, as runners navigate steep, rocky, and potentially..

The Kingman Farm Trail Race is a welcoming and challenging running event designed for participants of all skill levels. Spanning approximately 3.6 miles, the course features Nordic-style paths and switchback singletrack, making it an exciting experience for runners. This event is organized by acidot..

The People's Forest 7-Mile Trail Run is an annual trail running event held in Barkhamsted, Connecticut. It features a challenging 7-mile course through scenic forest trails, offering runners a chance to experience natural beauty and varied terrain. The race is part of the USATF Connecticut Mountain..

The Anchor Down Ultra is a seaside ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features multiple race options including 6-hour, 12-hour, and 24-hour ultra-marathons, catering to endurance runners of various levels. Known as "The Smallest State's Longest Races," it has b..

The Stonington Cross Country 5K is a free running event held at Stonington High School in Pawcatuck, Connecticut. The course begins with a loop on the school track, followed by a half-mile run on quiet, dead-end streets within the campus. Runners then transition to a mix of single- and double-track..

The GTA Challenge will take place in Greenfield on Saturday 16 August 2025.

The Tarc Summer Classic is a trail running event held at Noon Hill Reservation in Medfield, Massachusetts, featuring multiple race distances including 10 miles, 50K, and 40 miles. The course is a scenic, mostly forested loop with undulating terrain, roots, rocks, and a notable viewpoint at Noon Hill..

Greenbelt's Vineyard Hill Trail Run is an annual trail running event held in South Hamilton, Massachusetts, located on the scenic town line of Hamilton and Topsfield. The race offers 5K and 10K distances that challenge runners with a course featuring Vineyard Hill, sections of Bradley Palmer State P..

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.

Run for the Hills is an annual 5K trail run and walk held at the Oswegatchie Hills Nature Preserve in Niantic, Connecticut. The event offers participants a scenic course around Clark Pond and along the preserve's perimeter, showcasing over 450 acres of coastal forest. Designed as a fundraiser, proce..

The Wahaneeta Trail Run is a 5K trail race held in Westerly, Rhode Island, located on Moorhouse Road. Scheduled for September 13, 2025, it is the first event in the WTAC Fall Trail Race Series, which includes four races with a discount for registering in multiple events. This race embraces an "old s..

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Sunday 14 September 2025. You can run between 5 and 5 kilometers.

The Wine Run at Westport Rivers Vineyard & Winery is a scenic trail running event held in Westport, Massachusetts. The approximately 3-mile course winds through beautiful farms and finishes among the vineyard’s grapevines. After the run, participants enjoy a festive atmosphere with dinner, wine, and..