Trail Running calendar near East Hampton 2026-2027

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

Experience an empowering 5k obstacle mud run designed for women at Dorothy P. Flint 4-H Camp. Support sisterhood and breast cancer awareness while navigating a fun and muddy course in Riverhead.

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.

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..

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

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.

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 Roosevelt Forest on a 2.1 mile loop featuring classic New England terrain. Complete as many laps as you wish over 33 hours or aim for the 100 mile buckle in this intimate 50 runner event.

Test your endurance on a 4.25-mile loop in Hamden, CT. Set a goal from a marathon to 50 miles within the 12-hour window. Your registration supports local trail maintenance and comes with unique swag.

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.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

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..

The Rails-to-Trails 5K - East Hampton will take place in East Hampton on Friday 10 July 2026. You can run 5 kilometers.

Experience a midweek evening trail run through the diverse terrain of Bowdoin Park. This 5 mile race features a mix of grass and rocky trails with awards for top finishers and a food drive for the local pantry.

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 the wooded trails of the historic Ward Pound Ridge Reservation in New York. This event offers 25K, 50K, and 50 mile distances featuring a mix of technical singletrack and runnable carriage roads.

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.