Trail Running calendar near Stamford 2026-2027

Looped trail races in South Mountain Reservation offering distances from a kids 1-mile to a 50-mile ultra, with aid stations roughly every five miles and proceeds supporting the South Mountain Conservancy.

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 mountain trail event in Norvin Green State Park near West Milford, NJ, offering a 50K, 10 Miler and 5 Miler with substantial elevation gain, mandatory 50K gear, cupless aid stations and a one-dollar carbon offset added to regist..

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..

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.

Trail marathon and 15-mile trail race at Bethpage State Park on May 17, 2026. Registration opens Feb 23 and a portion of proceeds supports the Long Island Greenbelt Trail Conference.

A community campus event in East Haddam featuring a 1.75 mile looped course with rocky dirt paths, kids races on the soccer field, reused-trophy awards, dog-friendly provisions, and water stops on a rain or shine race day.

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 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..

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..

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.

Rise of the Obstacles in Wallkill NY is a two-day outdoor OCR event with a 100 m sprint, a two-lap endurance course, and kids' 50 m and 1 km races, featuring obstacle builds, finisher medals, and age-group awards.

The Tatum Classic is an inaugural trail race at Tatum Park in Middletown Township, NJ, run on a 4.75 mile repeatable loop with 1 lap, 30 kmish and 50 kmish options. Proceeds support MissionCleanWater's sustainable clean water projects.

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..

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.

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.

Join a unique non competitive group run along the D&R Canal Towpath with various distances and pace groups. Support the Rutgers Cancer Institute while running in a guided train formation to a celebratory picnic.