Trail Running calendar near Milford 2025-2026

Warm up your winter running at the Morris Hot Cocoa 5K and 10K in Morris Plains, NJ, a scenic grassy trail with rolling hills and postrace hot cocoa. Finishers get a medal and long sleeved shirt while proceeds support St. Jude Children's Re..

Take on the Holmdel Classic in Holmdel Park for a rugged trail challenge: choose the 50 km ish or the Halfish over multi lap loops that wind through roots, rocks and The Bowl. All proceeds support MissionCleanWater.

Enjoy a scenic trail challenge in South Mountain Reservation with looped 5K, 10K or 13.1M options over fire roads, single track and rolling hills. Aid stations are spaced about every three miles and participants receive a giveaway.

Celebrate the season at the Minty Miler in Jim Thorpe on Saturday December 13, 2025. This family friendly one hour run or walk loops Penn Forest Park with minty treats, mugs while supplies last, and age group awards.

Set sail for Blackbeard's Bounty Endurance Race in Pennsburg PA on December 20, 2025, and tackle timed 4 hour or 8 hour looped runs on scenic gravel trails. Enjoy pirate themed fun, post loop grog, and a race shirt and medal.

Run the Last Supper 100k in Roxbury NJ on Dec 27, starting at Horseshoe Lake. Choose solo or relay teams up to 10 and tackle scenic trails and lakeside roads for a winter ultramarathon adventure.

Hit the trails at South Mountain Reservation on January 10, 2026 for NJ Trail Series SOMO Winter 3, with 5K, 10K and 13.1 mile looped courses over hills and single track. Aid stations, on site registration and a giveaway add winter race day..

Join the ninth annual Frosty Fat Sass at South Mountain Reservation, a fundraiser for the South Mountain Conservancy. Choose a 5K, timed 3 or 6 hour loop or rucking division on a rugged, rocky 5K trail.

Hit the trails at the YETI OR NOT Snowshoe Invasion at Mountain Creek on January 31, 2026. Ride the lift to the top for a scenic 5k or untimed last mile welcoming runners, walkers and first time snowshoers. Bring your own snowshoes.

Join the Morris County Empanada Trail on March 29 in Morris Plains NJ with 5K and 10K runs over scenic mixed terrain. Entry includes a long sleeve shirt, finisher medal and an empanada with proceeds benefiting the Arthritis Foundation.

Squatchy Onesiefest 5K at Ramapo Valley is a festive trail run with a handcrafted finisher medal and awards for onesie wearers. Limited to 200, the flat gravel loop welcomes road shoes and offers aid and parking.

Join Febapple Frozen on Feb 21, 2026 in South Orange / Maplewood, NJ for a winter trail challenge on a 10 mile loop through South Mountain Reservation, with distances from 10 miles to 50 miles. Aid stations, official timing and event swag m..

Run or hike rugged woodland trails at the Mahlon Winter Donut Trail Run and Hike, with 5 and 10 mile options around Saffin's Pond. Trail markers keep you on course and the event runs rain, snow, or shine for a true winter adventure.

Squatchapple puts scenic singletrack and carriage road loops in South Mountain Reservation to the test with distances from 11 miles to 50 miles. Support the South Mountain Conservancy and earn a handcrafted wood medal and race swag.

Tackle a scenic 34 mile out and back along New Jersey's Lenape Trail, from South Mountain Reservation through Newark and back, with skyline views and varied terrain. This self supported adventure asks runners to carry their own gear and nut..

Take on MT. TAMMANY 10, an almost 40 mile looped trail challenge in the Delaware Water Gap with ten summit climbs and more than 10,000 feet of elevation gain. Technical, rugged terrain and river crossings make for a bold, scenic test.

Terror of Tammany! on March 22, 2026 in Columbia, NJ is a rugged looped trail challenge with 30K (three 6.7 mile loops) and 50K+ (five loops). Expect technical climbs, a campground start and finish, strict time limits, and finisher awards.

Explore rugged North Jersey wilderness in The Fools Adventure, a 10 hour foot ROGAINE with over 100 checkpoints across scenic, rocky terrain. Test your map and compass skills as you navigate for the best route and enjoy big views.

Tackle technical, rugged trails and steep climbs at Big Bear Squatch North in Bear Mountain NY on April 4, 2026. Choose a challenging 10K or a grueling half marathon, with proceeds supporting the New York New Jersey Trail Conference.

Scenic loop at Jacobsburg State Park on a 5 mile mix of single track and fast gravel. Choose single lap, 3 hour or 6 hour formats, bring your own hydration and enjoy a finisher pin plus sustainable medals supporting local conservation.