Trail Running calendar near Chesterfield 2026-2027

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.

Experience a 5K trail and obstacle run featuring 24 challenges across a 400 acre campus in Wallingford. This inclusive community event supports adaptive sports programs through a mix of wooded trails and open fields.

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

Trail races at Mansfield Hollow State Park include a roughly 15.7 mile out and back on the Nipmuck Trail and a new 5K single track loop; proceeds benefit Connecticut trail stewardship and the event is organized by the Shenipsit Striders.

A 53 mile ultramarathon across the Catskills from Windham to Phoenicia, with about 15,000 ft of climbing over rocky, steep trails. Limited aid stations require long self-sufficient stretches and a temporary waitlist registration process.

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Test your endurance at Elka Park with this 14.5 mile weighted event. Participants navigate over 5,000 feet of elevation gain while carrying a 20 pound pack through the New York landscape.

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 run and walk along the Black River in Springfield, VT, offering 7.4K and 4K options to benefit Springfield High School Cross Country. In-person and virtual entries, packet pick-up, refreshments, prizes, and family registration pricing are..

A trail event at Red Wing Recreation Area on July 5, 2026 offering 60K, 30K and 15K on a 15k loop with mixed surfaces, aid stations, lap-support for 60K runners, and awards for top finishers.

A multi-day loop event at Notchview in Windsor, MA featuring multiple timed and distance formats on a groomed 1.9 mile loop, on-course aid, campsite arrangements, and charitable donations to local beneficiaries.

Gather your team for a two day relay through the scenic Vermont countryside. Run flowy single track trails and camp under the stars at the Ascutney Outdoor Center for an unforgettable weekend of adventure.

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.

Muddy Princess Albany is a 5 km obstacle mud run for women held at Harley Rendezvous Classic Inc. Join this non competitive event focused on unity and empowerment while supporting the fight against breast cancer.

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.

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 a tactical mud run in Barre Massachusetts. Choose between a 5 to 7 mile course with 25 obstacles or a 3 mile sprint featuring 15 to 20 obstacles on a technical Saturday course.

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.

A forested 5K on the new trail network at Bridgewater Town Park in Bridgewater, CT on August 9, 2026. The course uses packed dirt and natural paths with gentle hills and views of Lake Lillinonah; participants receive a race-day gift.