Trail Running calendar near Milford 2026-2027

Trail event at Mahlon Dickerson Reservation on March 1, 2026 offering 5 mile and 10 mile routes over rugged woodland trails. Participants receive a long sleeved shirt, a medal, and donuts; hikers are welcome.

Squatchapple Trail Race The Squatchapple is a trail running and hiking event held at the South Mountain Reservation in West Orange, New Jersey. It offers four distances: an 11-mile, a 20-mile, a 50K, and a 50-mile race. The course consists..

A self supported, roughly 34 mile run along the Lenape Trail from Newark through parks and reservations to South Mountain Reservation. The route passes Branch Brook Park, Verona Park and Eagle Rock with varied trail surfaces.

The 14th annual Looney Leprechaun Trail Races offer a half marathon and a 10K on the trails of Tyler State Park. The event features age group awards and a t-shirt for early registrants. It's organized by trail runners for the trail running..

The Mt. Tammany 10 is a grueling 40-mile ultramarathon in New Jersey's Delaware Water Gap. Runners complete ten loops, each climbing over 1,000 feet to the summit of Mt. Tammany. This event promises tough, technical terrain with mountain vi..

Conquer the trails at Worthington State Forest in this arduous 30K or 50K+ event. Runners tackle a technical 6.7-mile loop with significant elevation. Finishers of both distances earn a commemorative award.

Run the historic 34-mile Lenape Trail from Newark to Millburn, traversing 18 parks. Choose to go solo or as a relay team, with full support including aid stations and shuttles. This charity event supports MissionCleanWater's work to provide..

Trail 5K and 10K events in Central Park of Morris County on March 29, 2026, featuring mixed-terrain cross country courses. Entry includes a long-sleeve shirt, finisher medal, and an empanada with a vegetarian option.

The Fool's Adventure is a ten hour foot rogaine on March 29, 2026 in Wayne, New Jersey. Competitors navigate more than 100 checkpoints across eight square miles of rugged wilderness using maps and a compass while recording checkpoint eviden..

Run a rugged 10k trail race through the historic paths of Van Cortlandt Park in the Bronx. It's billed as the first true five-borough trail run. Finish line prizes include famous carrot cake, and part of your fee supports local park trails.

Tackle the rugged trails of Harriman State Park in this mountain trail run. Choose between a challenging 10K with 1,400 feet of climb or a half marathon with over 2,600 feet. The event supports local trail maintenance and includes a rucking..

Timed loop trail races at South Mountain Reservation in South Orange on April 4, 2026. Options include a 1.88 mile loop, a 6K two loop option, and 1 hour, 3 hour and 6 hour timed events.

The Long Run - Spring Forward offers trail runs in Jacobsburg State Park. Choose from a 5-mile loop, a 3-hour, or a 6-hour timed event on mixed terrain. It's a cupless, eco-conscious event supporting the local environmental center.

An Easter-themed 5K on April 4, 2026 in Shickshinny, PA, held on a flat out and back course along the Susquehanna Warrior Trail. The event features souvenir T-shirts, age-group awards, photos with the Easter Bunny, and lunch.

A 6K trail event in Institute Woods, Princeton, on maintained natural-surface trails. A non-competitive 3K option is available for slower paces and post-run refreshments are provided.

A community trail event in Cross River, NY on April 12, 2026 featuring a 5k trail race, a 4k walk that skips part of the hill loop, and a 200 meter kids dash on the track.

Tackle the private singletrack trails of Forever Farm in Mertztown. Choose from a 5k, 10k, half marathon, marathon, or a unique team ultra relay. Enjoy free camping, a post race meal, and a finisher award.

A 5K race winds through Heckscher Farm and forest trails at the Stamford Museum and Nature Center. Children can join a short fun run past friendly farm animals. The event offers a unique running experience surrounded by nature.

The Fifth Street Rock Monster is a technical trail event on the private singletrack of Forever Farm. The 2026 edition features a new continuous loop course across five distances, camping, and a post race meal.

A community trail event in Irvington on April 12, 2026 featuring a 5k trail run and a 0.6 mile kids 1K for ages 10 and under, with a portion of proceeds supporting the Irvington Bulldog Booster Club.