Trail Running calendar near Roxbury 2026-2027

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 weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

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.

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..

Experience a technical seventeen mile trail run along the Hudson River cliffs with over five thousand feet of elevation change. High endurance is required for this rugged course featuring boulder scrambles and scenic river views.

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.

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.

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.

Explore the varied trails of Fahnestock State Park in New York with a choice of 50K, 25K, or 5.5-mile races. The event includes course support, a post-race meal, and supports park conservation through its non-profit organizer.

Climb It For Climate is a trail running event on Belleayre Mountain in the Catskills, offering 25K and 8K race options. The weekend features pre-race activities, and the event focuses on environmental responsibility with a zero-carbon initi..

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.

Experience Stratford’s dirty day on the beach at this 5k obstacle race featuring 18+ challenges through sand and water to support the Sterling Community Center.

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.

Explore the scenic Shawangunk Ridge on a rugged 70-mile trail. Choose from three distances: a 70-miler, 30-miler, or half marathon. This unsupported event celebrates the preserved beauty of the 'Gunks' mountains.

The City Challenge Race returns for its 12th year on the Jersey City waterfront. This is the only event of 2026, featuring a fast 3-mile urban obstacle course with over 20 unique challenges. Participants receive finisher medals, professiona..

Experience a diverse trail race at South Mountain Reservation featuring fire roads and single track trails. Choose from multiple distances ranging from a 5K to 50 miles with aid stations every three miles.

Experience the rugged beauty of northwest Connecticut at Macedonia Brook State Park. Featuring single track trails and views of the Catskill Mountains, this event offers 12K, 25K, and 50K distances for trail runners.