Trail Running calendar near Sterling 2026-2027

A lap-based 100-mile trail event at Roosevelt Forest in Stratford, CT, with a 33-hour cutoff and a field limited to 50 runners. The course features New England single and double track, a single pavilion aid station, and pacer rules.

Experience an obstacle course weekend at a lush Massachusetts farm featuring rolling hills and mud. Choose from 5k and 10k races or the kids division with onsite farm treats and a local brewery.

A point to point 5K in East Hampton that starts at the Connecticut Draft Horse Rescue and finishes at the Old Home Days grounds. Shuttle buses serve the start, pre registration includes a 2026 T shirt and walkers are welcome.

The TARC Blue Hills Skyline Trail Run will take place in Canton on Saturday 11 July 2026. You can run 12 kilometers.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.

A one-mile out-and-back on the Farmington Canal Heritage Trail in East Granby, offered in two waves and hand timed, on crushed gravel. Limited parking and a $25 registration fee; all proceeds benefit charities.

Test your endurance at Soapstone Mountain with a five point five mile circuit featuring six mountain ascents. Run through rocky trails and finish at the mountain tower in Shenipsit State Forest.

Experience an obstacle course with over a dozen mud pits at the 508 INTL Adventure Sports Center. Enjoy a non competitive environment featuring music, food, and a festive atmosphere for both participants and spectators.

An evening cross-country event at Stonington High School on August 5, 2026, featuring a 5K and a Children's 1/2 Mile for ages 10 and under. The course starts and finishes on the track and includes campus streets, trails, grass, and a bridge..

The Tarc Summer Classic will take place in Medfield on Saturday 8 August 2026. You can run between 10 and 40 miles.

The Running Wild at Wildwood Trail 2.5 Mile Trail Run/Walk will take place in Wading River on Saturday 8 August 2026. You can run 3 miles.

A community eight hour trail event of roughly 5K loops at Crandall's Park in Tolland, CT on August 15, 2026. The day includes a potluck, raffles per loop with prizes, and a 50th anniversary gift for runners who complete at least one loop.

Experience a scenic off-road trail run or walk through the conservation lands of White Barn Farm. This cup-less 5k event supports local sustainable agriculture and community food security in Wrentham.

Experience a classic 5k cross country race through the scenic fields of Waters Farm in Sutton. Join the USATF New England Grand Prix season opener on a spike friendly course with both open and masters divisions.

Ocean State Ultra is a loop trail event at Big River Management Area in West Greenwich, Rhode Island offering 100 mile, 12 hour and 6 hour races. The course uses 10 mile loops with trails, short pavement sections, and staffed aid stations.

Traverse the scenic ski slopes and forest trails of Wachusett Mountain in this timed event featuring loops from 7 to 28 miles. Earn a finisher medal within 10 hours and enjoy a post trek party at the mountain base.

A family friendly 5k obstacle race at Stratford Short Beach on September 5, 2026, featuring more than 18 obstacles with sand and water elements. The event raises funds for Sterling Community Center programs and supports team and individual..

Experience a scenic 3.3 mile trail run or hike through the Oswegatchie Hills Nature Preserve. Support local land conservation while enjoying a timed course around Clark Pond followed by an awards ceremony with refreshments.

The TARC Fall Classic will take place in Carlisle on Saturday 5 September 2026. You can run between 10 and 50 miles.

The Veterans Count Nashua 5k Fun Run & Walk will take place in Nashua on Saturday 5 September 2026. You can run 5 kilometers.