Trail Running calendar near South Orange 2025-2026

The New Paltz Pizza Challenge is a fun and unique 3.3-mile running event held in New Paltz, NY, starting at Water Street Market. The course is approximately 5 kilometers and offers participants a lively atmosphere with plenty of pizza to enjoy along the way. The event features prizes for the winners..

The Dirty Dozen 50K is a challenging ultramarathon held in Forest Park, Queens, New York City. The race features a 2.5-mile loop along the scenic Orange Trail, completed 12 times for a total of 50 kilometers. Each loop includes 300 feet of elevation gain, making the course deceptively tough with rol..

Raptor Ridge, presented by Peace, Love, Trails (formerly the Sanctuary 6.5), is a 6.5-mile trail race held at Westmoreland Sanctuary in Westchester County, New York. The route weaves through the sanctuary’s rugged, scenic trails across 669 acres and 8.5 miles of hiking trails. Start and finish are a..

The USATF-NJ Open & Masters 5k Cross Country Championships is a competitive running event held at Natirar Park in Peapack Gladstone, New Jersey. Scheduled for August 24, 2025, this 5-kilometer cross country race features divisions for both open and masters athletes. It is part of the Paul Miller Aut..

The Barn-B-Q Trail Festival, held in Berkeley Heights, NJ, is a unique outdoor event combining trail running, hiking, and a lively barn party. Set in the historic Deserted Village of Feltville within Watchung Reservation, participants can enjoy self-guided trail tours ranging from 2 to 6 miles, with..

The FallApple is a trail running event held in South Orange, New Jersey, at South Mountain Reservation. Scheduled for early September, the race offers a variety of distances including 5K, 10K, half marathon, marathon, 50K, and 50-mile options. The course features a mix of fire roads, single-track tr..

10K Run for the Osprey is a fall running event at Lacawac Sanctuary in Lake Ariel, PA (William E. Chatlos Environmental Education Center, 182 Sanctuary Road). The event offers a 10K Trail Run and a 5K Walk.The course is described as scenic, winding through diverse landscapes to support habitat conse..

Macedonia Trail Race, staged at Macedonia Brook State Park in Kent, CT, offers 12K, 25K, and 50K distances through unparalleled single-track and lush forest trails. The course features grinding climbs, technical descents, and several viewpoints, including Cobble Mountain with an overlook where, on c..

The Storybook Half Marathon is a scenic 13.1-mile trail race held in Roosevelt Forest, Stratford, Connecticut. The course consists of eight loops on a 1.64-mile wooded trail featuring singletrack and doubletrack paths with roots, rocks, and gentle hills, offering a charming yet moderately challengin..

The Mountain Lakes Trail Run & Walk in Princeton, NJ, is a scenic event held at the Billy Johnson Mountain Lakes Nature Preserve, benefiting the Friends of Princeton Open Space. The event features a 5K+ trail run and a 3K walk, with the run course consisting of about 10% paved trails, 30% unimproved..

Located at Lakeside Park in Pawling, New York, the Pawling 24 Hour Trail Running Festival is the sixth edition of the endurance event, offering 24-, 12-, 6-, and 3-hour races (including a 12-hour night start). Runners tackle a 1.68-mile loop made up of pavement, grass, and single-track, with about 1..

The 2025 Boxers' Trail 5K (Run and Walk) is an in-person event in Philadelphia, PA, scheduled for Saturday, September 13, 2025, at Mander Playground (2140 N. 33rd St). Participants can choose the Boxers' Trail 5K Run, 5K Walk, or the Boxers' Trail 5K Youth option for ages 13–17.The course winds thro..

2025 Hellbender Hustle (and Dragonfly Dash) is a 5-mile trail run/walk around Leaser Lake in Lehigh County, near New Tripoli, PA 18066. The event spotlights the Eastern Hellbender—North America’s largest salamander and Pennsylvania’s state amphibian—with a ~100-yard Dragonfly Dash youth sprint to st..

The Where the Pavement Ends Single & Double Loop is a trail running event held in Ridgefield, Connecticut, starting and finishing at the Lake Windwing ballfields. Scheduled for September 14, 2025, the race offers two options: a 4.25-mile single loop and an approximate 8-mile double loop through the..

The Wild Goose Trail Festival takes place at Wawayanda State Park in Hewitt, New Jersey, offering a variety of trail running events over September 20-21, 2025. Distances range from a 1-mile kids run to a challenging 100-mile ultramarathon with a generous 36-hour cutoff, making it ideal for first-tim..

The Gardiner Dump Run is a scenic trail running event held in Gardiner, New York, featuring a 5k race with an option to complete two laps for a 10k distance. The course winds through single-track trails along wooded hillsides near the Wallkill River and untamed fields at Gardiner’s Riverbend Trails,..

The Caldwell Cougar Chase 5K and 8K will take place in Woodland Park on Saturday 27 September 2025. You can run between 5 and 8 kilometers.

Water Gap 50k and Half takes place in Milford, Pennsylvania, within the Delaware Water Gap National Recreation Area. The event offers 50K and 25K distances, with the McDade Trail serving as the course—a 32-mile point-to-point route through the Gap, mixing rail-trail cinder paths with rolling singlet..

Cedar Run's Trails, Tails & Ales is an annual 5K charity trail run held at Woodford Cedar Run Wildlife Refuge in Medford, New Jersey. The event features a scenic, exclusive trail course starting and ending at the Nature Center Pavilion. Participants receive a limited edition event t-shirt, light bit..

Front Runners New York's Cross Country 5K returns to Van Cortlandt Park in the Bronx for its 22nd annual fall meet. The Run/Walk begins near the Tortoise & Hare Sculpture, with bib pickup guided by FRNY volunteers. Supported by the Tom Cook Fund, race-day amenities include on-site registration, swag..