Trail Running calendar near Northampton 2026-2027

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.

The Red Wing Trail Challenge offers 60K, 30K, and 15K distances on a rugged 15K loop in Lagrangeville, NY. The course features mixed terrain and significant elevation gain on each lap. Post-race food and unique finisher awards are provided.

Notchview Ultra features a 1.9-mile groomed loop trail in Windsor, Massachusetts. The event includes multiple ultra distances from 6 to 72 hours and a 100.7-mile race. Proceeds support the Trustees of Reservations and a local humane society..

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.

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.

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.

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..

Test your endurance on a 0.355-mile track loop for 8 hours at Clapp Park. Enjoy a unique bottle-drop aid station and support the AYJ Fund for children with cancer. Awards celebrate all age groups and lifetime achievements.

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..

Lover's Lane is a timed trail run on a 1.8-mile loop in Chester, VT. Participants can choose 6-hour or 12-hour options in a community-supported, fat-ass format. The event supports local recreation and recovery services.

Explore the new trails of Bridgewater Town Park at the Tappen Brook 5K. This community trail run on August 9, 2026, offers a scenic course through woodlands with views of Lake Lillinonah. Participants receive a gift, and top finishers win p..

Join an 8-hour celebration run on a 5K trail loop in Tolland, CT. Earn raffle tickets for each loop and enjoy a community potluck. All participants receive a special 50th-anniversary gift.

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.

Run the Jug End Loop Ultra in the scenic Jug End State Reservation. Choose between a 4.2-mile race or a 6-hour ultramarathon on a challenging loop trail. All finishers receive a handmade ceramic mug, and the event supports local charities.

This 4-mile trail run in Schenectady Central Park uses a flexible time trial format. All proceeds support addiction recovery services, honoring a personal legacy. A pre race stretching session is included.

Experience a scenic trail festival at Thacher State Park featuring races from 10k to 50k miles. Run through wide paths and single track trails with beautiful escarpment views in a sustainable cupless event.

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.