Trail Running calendar near Edgartown 2025-2026

The Anchor Down Ultra is a seaside ultra-marathon event held at Colt State Park in Bristol, Rhode Island. It features multiple timed race options including 6-hour, 12-hour, and 24-hour ultra-marathons. Known as "The Smallest State's Longest Races," this event has been recognized by Men's Health Maga..

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 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..

The Watermelon Wobbler 5k is a fun, off-road trail run held at White Barn Farm in Wrentham, Massachusetts. This 5K race takes participants through scenic conservation land and farm property, featuring dirt and gravel paths with natural obstacles like rocks, roots, and elevation changes. Open to all..

The Foot It for Felix 5K is a scenic running and walking event held at Felix Neck Wildlife Sanctuary in Edgartown, Massachusetts. Participants traverse beautiful nature trails featuring pine needle-covered paths, fields of goldenrod, and stunning views of Sengekontacket Pond and State Beach. The cou..

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 Wine Run at Westport Rivers Vineyard & Winery is a scenic trail running event held in Westport, Massachusetts. Scheduled for September 14, 2025, the race features a roughly 3-mile course winding through picturesque farms and vineyards. Participants enjoy a relaxed atmosphere with professional ti..

The Charlie Stavros Memorial Beach Run is a free, 3-mile race held at Westerly Town Beach in Westerly, Rhode Island. Organized by the Westerly Track Club and the Stavros family, this event takes place at low tide, featuring a scenic out-and-back course of 1.5 miles each way along the beach. The run..

The Survival of the F.I.T.test - 30+ Hour Trail Ultra is a challenging endurance event held in Cumberland, Rhode Island. Participants can choose between two course options: a flat, fast 2.1-mile loop or a more rugged 4.2-mile trail loop used in previous years. The event offers multiple race formats..

The Moosup Valley 5K and 10K All Trail Race takes place in Moosup, Connecticut, on the newly restored Moosup Valley State Park Trail. This event features a 5K, a 10K, and a Kids Fun Run, all held on a 100% trail course that crosses only one dead-end road. The race starts and finishes at the Griswold..

The Run for the Pumpkins Trail Run, held in Westerly, Rhode Island at Bradford Preserve, is part of the WTAC Fall Race Series. This event features 5K and 10K trail races, along with a free 1K children's run for ages 10 and under. The courses highlight preserved town land and the Woody Hill Managemen..

The CFA Trail 5K & Children's Fun Run for Mental Health is a timed trail running event held at Deans Mill Farm in Stonington, Connecticut. Participants can choose between a 5K trail run or a fun run for children aged six and under. The race takes place amid beautiful fall foliage, offering a scenic..

The North Kingstown Firefighters Association Blazing Trail 5K is a trail run/walk event held at Ryan Park on Oakhill Road in North Kingstown, Rhode Island. This scenic 5K course offers participants a chance to enjoy the natural beauty of Ryan Park while supporting a good cause. Proceeds from the eve..

The Aggie Ram Trail Run 5k will take place in Walpole on Sunday 5 October 2025. You can run between 5 and 5 kilometers.

The Houghton's Pond Trail Races take place in the scenic DCR Blue Hills Reservation in Milton, Massachusetts, just south of Boston. This event offers two trail race distances: 7 miles and 3.7 miles, both starting and finishing near the Houghton's Pond Visitor Center. The courses feature rolling terr..

The WWII Veterans Memorial Trail Weighted Race is a unique endurance event held in Mansfield, Massachusetts, on a 2.5-mile out-and-back rail trail featuring paved, gravel, and grass surfaces. Participants have six hours to complete as many laps as possible while carrying weighted packs, with their s..

The Weir River Farm Trail Race, held annually in Hingham, Massachusetts, offers runners three trail distances: 10 miles, 6 miles, and 3.4 miles. The race courses wind through the scenic trails of Weir River Farm, Whitney, and Thayer Woods, with the 10-mile route including additional loops in Wompatu..

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

Womp Romp is an annual trail running event held at Wompatuck State Park in Hingham, Massachusetts, featuring a 10-mile single-loop race and a 50K race consisting of three loops plus an additional mile. The course offers a mix of single track, wide trails, and some paved sections, suitable for both n..

The Pumpkin Pacer 5k at White Barn Farm in Wrentham, Massachusetts, is a scenic trail run/walk/hike held annually in late October. This off-road 5K course features dirt and gravel paths with natural terrain including rocks, roots, and elevation changes, offering a fun challenge for all ages and skil..