Trail Running calendar near Charlestown 2026-2027

A community 5K trail run, walk and hike in Eisenhower Park Milford on June 7, 2026 supporting the Milford Rotary and the Beth El Center. The course uses a high school cross country route with mostly flat sections and some rolling hills.

Trail action at Mansfield Hollow State Park with a scenic yet challenging 15 Miler along the Nipmuck Trail and a new technical 5K inside the park. Expect river views, woods, bridges and climbs while supporting Connecticut trail stewardship..

Early morning trail run in Gay City State Park offering 3, 5 and 8 mile races. The 8 mile is part of the Blue Blazed and USATF CT MUT series and includes teams of three competing for prize money.

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

A 5.5 mile trail race at Soapstone Mountain featuring six ascents and about 1500 feet of climbing. The route circles the mountain with multiple steep rocky sections, limited aid access, and a field limited to 50 runners due to parking.

Run the Stonington Cross Country 5K in Pawcatuck at Stonington High School on Wednesday August 5. The scenic course starts and finishes on the track and winds through quiet streets, trails and grassy crossings for a community run.

Experience the Trail Animals Running Club Summer Classic at Medfield's Noon Hill and Shattuck Reservations, a scenic and challenging 10 mile loop of forested singletrack that climbs to a Noon Hill vista. Distances include 10 miles, 40 miles..

Run loops on a roughly 5K trail course during an eight hour celebration with the Shenipsit Striders in Tolland. Bring food, enjoy the grill, earn raffle tickets and a 50th anniversary gift while supporting local trail stewardship.

Run the Old Goat Track Club XC Classic at Waters Farm in Sutton, a spike friendly 5K cross country loop and USATF New England Grand Prix stop. Perfect for teams and individual racers, with finish line snacks and a nearby after party.

Run for The Hills is a 4th annual trail 5K on September 12, 2026 at Oswegatchie Hills Nature Preserve, winding around Clark Pond. Expect exposed rocks and roots on scenic trails while helping support preserve maintenance.

Join the Charlie Stavros Memorial Beach Run on September 15, 2026 in Westerly, Rhode Island, a free 3 mile beach run honoring a beloved local runner. Enjoy a scenic low tide out and back along Westerly Town Beach with friends and family.

The Ocean State XC Invitational will take place in East Greenwich on Saturday 26 September 2026. You can run 5 kilometers.

Run the newly restored Moosup Valley State Park Trail in Moosup CT with 5K, 10K and a kids fun run on Sunday September 27, 2026. Postrace medallions or tee shirts, food and drink, leashed dogs welcome, and proceeds benefit the Rotary Club o..

The Run for the Pumpkins Trail Run will take place in Misquamicut on Saturday 3 October 2026. You can run between 5 and 10 kilometers.

Tackle a scenic 5K or 8K through Pindar Vineyards on flat packed trails while supporting the NY Cancer Foundation. Finish with live music, food trucks and a complimentary glass of Pindar wine for a festive fall celebration.

Take on the NipMuck Trail Marathon in Ashford CT on October 4, 2026, a rugged 26.4 miles out and back across rocks, roots, mud and scenic wood bridges. Organized by the Shenipsit Striders, the race supports Connecticut trail stewardship.

A series of trail races in Rocky Point NY using a 10.48 mile loop repeated for distances from 10 mile to 150 mile. Two aid stations provide Hylē Hydration and food, and some distances include night race options.

Join the 20th Wayland / HFC Striders Cross Country Festival on October 11, 2026, featuring youth 3K races and open 5K events that support Wayland High School cross country and track. Presented by Middlesex Savings Bank with awards and commu..

Enjoy a scenic 3 mile trail at Sakonnet Vineyard, then celebrate with wine, dinner, music and a souvenir wine glass. BBQ only and kids BBQ options are available for those who prefer to skip the run.

Point to point trail race in Northeast Connecticut on October 17, 2026, running through the Air Line Trail State Park from Willimantic to Putnam. Offers marathon, half marathon, 10K, and a marathon relay with proceeds supporting local stude..