Trail Running calendar near Westport 2025-2026

The 7-11 Slurpee Day Ultra 60k is a unique running event taking place in Vernon, CT, on July 11, 2025. Participants will cover a distance of 37.5 miles, primarily on roads, while making stops at various 7-11 locations along the route. This self-supported run encourages camaraderie and fun, with a so..

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 Anchor Down Ultra is a premier ultra-marathon event held at Colt State Park in Bristol, Rhode Island. This seaside race features three distinct events: a 6-hour, a 12-hour, and a 24-hour ultra-marathon, catering to various levels of endurance runners. Recognized as one of the "Best Races in Amer..

The Stonington Cross Country 5K is a running event scheduled for August 13, 2025, in Pawcatuck, Connecticut. This event features a 5K race along with a Children's 1/2 Mile, catering to young participants aged 10 and under. The race begins on the track at Stonington High School, followed by a scenic..

The Tarc Summer Classic will take place in Medfield on Saturday 16 August 2025. You can run between 10 and 40 miles.

The Vineyard Hill Trail Run, organized by Greenbelt, is an annual running event featuring 5K and 10K trail races. Set in the scenic areas of Hamilton and Topsfield, Massachusetts, the course includes challenging terrain over Vineyard Hill, sections of Bradley Palmer State Park, and the Bay Circuit T..

The TARC Fall Classic will take place in Carlisle on Saturday 6 September 2025. You can run between 10 and 50 miles.

The Wahaneeta Trail Run is a 5K trail race taking place in Westerly, Rhode Island, as part of the WTAC Fall Race Series. This event emphasizes a "no frills" approach, foregoing modern amenities like t-shirts and extensive awards to keep costs low and logistics simple. Participants can enjoy a classi..

The Wine Run at Westport Rivers Vineyard & Winery is a scenic running event scheduled for September 14, 2025, in Westport, MA. Participants can enjoy a beautiful trail run through the vineyard, covering approximately 3 miles amidst picturesque farms and vines. After the race, attendees can indulge i..

The Charlie Stavros Memorial Beach Run is a free, end-of-summer 3-mile running event held at Westerly Town Beach, Rhode Island. Organized by the Westerly Track Club and the Stavros family, the race features a scenic route that includes a 1.5-mile out-and-back course along the beach at low tide. This..

The Cockaponsett Trails to a Cure is a running event taking place in Chester, Connecticut, featuring two trail races: a 4-mile and a 9-mile course through the scenic Cockaponsett State Forest. The course includes challenging terrain with roots, rocks, and hills, and is designed to accommodate runner..

Run for Nature is a community-focused running event taking place at Shedd Park in Lowell, MA, on September 28, 2025. Participants can choose from a 5K Run/Walk, a 10K Trail Run, or a Kids 1-Mile Fun Run. The event aims to support the Lowell Parks and Conservation Trust's efforts in conservation and..

The Run for the Pumpkins Trail Run is part of the WTAC Fall Race Series, taking place at Bradford Preserve in Westerly, Rhode Island. Scheduled for October 4, 2025, the event features a 10K, a 5K, and a children's 1K run for participants aged 10 and under. The courses showcase the natural beauty of..

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 Houghton's Pond Trail Races feature two distances: a 7-mile race and a 3.7-mile race, set in the scenic DCR Blue Hills Reservation in Milton, MA. Participants will navigate rolling dirt roads and forest paths, with elevation changes of approximately 700 feet for the 7-mile course and 300 feet fo..

The Weir River Farm Trail Race, scheduled for October 19, 2025, in Hingham, MA, features three race distances: 10 miles, 6.0 miles, and 3.4 miles. This annual event showcases the scenic trails of Weir River Farm and the surrounding Whitney and Thayer Woods. Participants can enjoy post-race cider don..

The Grills Trail Run is a running event taking place at Grills Preserve in Westerly, Rhode Island, as part of the WTAC Fall Race Series. Participants can choose between a 10-mile and a 10K course, both of which feature scenic trails, bridges, and riverfront views within the Grills Wildlife Sanctuary..

Womp Romp is an exciting running event taking place in Wompatuck State Park, Hingham, MA, featuring a 50K and a 10-mile race. Celebrating its fifth year, the event has consistently sold out, with a cap of 350 participants. The course includes a mix of single track, wide trails, and pavement, caterin..

The Powisset Farm Trail Run - Fall is a part of the Barn to Run Trail Race Series, taking place at Powisset Farm in Dover, MA. This event features four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, catering to both experienced and novice trail runners. Participants can enjoy post-r..