Trail Running calendar near West Rock 2026-2027

A trail running event at Ward Pound Ridge Reservation offering 25K, 50K and 50M courses across wooded singletrack and carriage roads with runnable sections, ridge views, aid stations, and GPX course files.

The Muddy Dash - Boston will take place in Charlton on Saturday 1 August 2026.

A community cross country meet at Stonington High School offering a 5K and a children's 1/2 mile. The course mixes track, quiet campus streets, trails, grass, and finishes back on the track.

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.

An 8 hour track ultramarathon at Clapp Park in Pittsfield on a certified 0.355 mile dirt and cinder loop with chip timing, a bottle drop aid system, age group awards, and proceeds benefiting the AYJ Fund.

A 2.5 mile trail run at Wildwood State Park on August 8, 2026. The rain or shine event offers live results and free finish line photos and benefits the Friends of Wildwood State Park.

A short trail 5K through recently developed forested trails at Bridgewater Town Park on August 9, 2026. The third annual race is organized by The Bridgewater Land Trust and the Bridgewater Recreation Commission and includes participation gi..

Step Up for the Brave runs Aug 10–15, 2026 with 90 minute stair climb and walk challenges at Sacred Heart University plus a five day 40,000 step virtual challenge supporting veterans experiencing homelessness.

A community potluck and trail run in Tolland, CT on August 15, 2026. Participants run 5K loops during an eight hour period, earn raffle tickets per loop, and receive a 50th anniversary gift after completing a loop.

Trail races in Fahnestock State Park near Cold Spring, NY on August 15, 2026, offering 50K, 25K and a 5.5-mile option across mixed dirt roads and single track. On-course aid and post-race meal included; proceeds support park conservation.

A timed 5K at Brimfield Winery on August 15, 2026, run on a mostly grass cross country style course. Registration options include a standard 5K with a postrace wine pour and a volunteer plus run option.

A timed six hour ultramarathon on a 4.2 mile loop at Jug End State Reservation in Egremont, MA. The wooded course includes fields and an apple orchard and benefits the Louison House.

On August 23, 2026 Raptor Ridge stages a 6.5 mile trail race at Westmoreland Sanctuary in Mount Kisco, New York. The event starts and finishes at the Fox Lane High School campus, dogs are not allowed and non perishable food donations are co..

A multi event ultramarathon in West Greenwich, Rhode Island featuring a repeated 10 mile loop with desert, pavement and trail sections. Chip timed events include aid stations, a finisher sweatshirt and a buckle for 100 mile finishers.

A 50K in Forest Park Queens run as 12 laps of a 2.5 mile Orange Trail loop, each lap adding about 300 feet of climb and with aid stations after every circuit. The event combines a grassroots race atmosphere with an 8 hour cutoff.

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 family friendly beach 5k obstacle race in Stratford each September, featuring 18 plus obstacles and community fundraising for Sterling Community Center programs. Participants and teams raise funds while running, walking, or navigating obs..

A trail event on the Shawangunk Ridge near Rosendale offering 70 mile, 30 mile, and half marathon divisions over rugged, minimally supported terrain with shuttle logistics and enforced checkpoints.

An urban obstacle race on the Jersey City waterfront on September 12, 2026. The event features a fast 3 mile course with 20 plus city-style obstacles, chip timing, new finisher medals, awards, and free race photos.

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.