Trail Running calendar near Waterbury 2026-2027

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.

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.

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 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.

A loop-based trail event at Crandall's Park on August 15, 2026 featuring roughly 5K loops, potluck food, raffles with tickets earned per loop, hidden treasures on course, and a 50th anniversary gift for anyone who runs a loop.

Trail races at Fahnestock State Park in Cold Spring NY on August 15, 2026 offer three distances across varied terrain with aid stations, a post race meal, and proceeds supporting land conservation.

A six hour lap ultra on a 4.2 mile wooded and orchard course at Jug End State Reservation on August 22, 2026, featuring 830 feet of elevation change per lap and a 0.75 mile mini loop in the final hour; proceeds benefit Louison House.

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.

A 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco on August 23, 2026, with start and finish at the Fox Lane High School campus and a non-perishable food collection for the Mt. Kisco Food Pantry.

Ocean State Ultra on August 29, 2026 in West Greenwich, Rhode Island offers 100 mile, 12 hour and 6 hour loop races on 10 mile laps through Big River Management Area with aid stations and shuttle supported parking. 100 mile finishers receiv..

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.

A trail event near Rosendale New York with 70 mile, 30 mile, and half marathon options along the Shawangunk Ridge. The course is rugged and minimally supported so participants must carry food and water purification.

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..

Trail race at Macedonia Brook State Park on 13 September 2026 featuring single-track forest trails, climbs, viewpoints and three distances: 50K, 25K and 12K.

The Corporate Fun Run Pier 84 Manhattan will take place in New York on Monday 14 September 2026. You can run 5 kilometers.