Trail Running calendar near Waterbury 2026-2027

A trail event at Pittsfield State Park offering 50K, 25K and a 5-mile loop with two aid stations and nearby camping; organized by BURCS and supporting three regional animal rescue groups.

Experience a scenic trail run through the meadows and forests of Muscoot Farm. Choose from the 5 mile course or youth races and receive vouchers to spend at the local farmers market.

A technical trail race in Norvin Green State Park offering 50K, 10 Miler and 5 Miler courses over steep terrain, boulder fields and river crossings. The event is cupless, has aid stations and specific mandatory gear for the 50K.

Celebrate a Hudson Valley tradition dating back to 1983 with the Run Like The Wind 5K in Ellenville. This scenic course runs along the Shawangunk Mountains and features a section on the newly resurfaced Rail Trail. All event proceeds suppor..

New for 2026, the Soapstone Mountain Trail Races in Stafford Springs feature an all new half marathon route over Soapstone Mountain and a Jerry Stage 6K sampler, both running on sections of the blue-blazed Shenipsit Trail with proceeds to l..

Run a 3.5-mile trail race in Wolcott, CT. The event supports the local cross country teams. Your entry includes access to the CT Food Truck Battles Festival afterward.

Experience Long Island trail running with a full marathon or 15 mile race at Bethpage State Park. Support the local Greenbelt Trail Conference while exploring the natural paths of Farmingdale.

Experience a refreshing spring trail run or walk through the scenic paths of Blydenburgh County Park. Enjoy a 5K course featuring dirt roads and wooded trails followed by delicious refreshments and professional finish line photos.

Mine Hill Half Marathon is a 13.1 mile road race in Roxbury, Connecticut, with start and finish at Mine Hill Distillery. The course passes farms, fields and scenic vistas and includes a post-race gathering at the distillery.

A 4 mile out-and-back road and trail race in Forest Park, Queens on May 24, 2026, starting and finishing at Victory Field Track; entries capped at 500, guaranteed technical shirts for pre-registrants, custom medals for finishers and cash aw..

ENDURE is a Last Man Standing running event where participants complete a fixed loop every hour. The last runner standing wins, with a central hub for recovery and community. It's designed for all levels, from seasoned endurance athletes to..

Experience a 5K cross country run or walk through the mowed trails of Peach Hill Park. Reach the highest point in Poughkeepsie for panoramic views and enjoy post race snacks and awards.

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

Test your skill and grit at a permanent outdoor obstacle facility in Wallkill. Explore a variety of competitive sprints and non-competitive endurance courses for both adults and children over a two-day weekend.

Test your limits at this multi day vertical endurance series at Mohawk Mountain. Choose from seven elevation based challenges ranging from 12 to 84 hours as an individual or part of a flexible relay team.

A point-to-point trail event on the New England Trail offering 112-mile and 50-mile options. Entrants must donate to the Connecticut Forest and Parks Association and provide proof; runners must self-navigate and arrange crew support.

Experience a timed 5K trail run or walk through the scenic woods and fields of the Van Vleck Farm and Nature Sanctuary. Enjoy live music and food trucks at this annual community event in Woodbury.

The Rockwood Ramble 10K offers a scenic run on carriage roads through the woods of Rockefeller State Park Preserve. The event features a standard 10K and a separate kids' run, with all proceeds supporting trail maintenance.

The Levee Loop Trail Race 10K - Islip will take place in Islip on Saturday 6 June 2026. You can run between 5 and 10 kilometers.

Paired 5K paved loop and 10K mountain trail at Rockland Lake State Park in Valley Cottage, NY. The 5K is a flat, fully accessible lake loop; the 10K climbs about 1,300 ft on rocky, steep terrain and includes one aid station.