Trail Running calendar near Milford 2026-2027

A community trail event on May 9, 2026 in Orangeburg NY offering looped courses of 3.75, 7.5, and 11.25 miles to support Rex Runs Kindly and NAMI of Rockland, with aid stations and participant T shirt and medal.

Experience Trails To the Sky at Voorhees State Park with a UTMB Index 50k of five scenic laps or a spirited 10k, winding past the park observatory. Aid stations and custom finisher medals round out this classic trail race.

A spring trail event at Muscoot Farm in Katonah, NY on May 17, 2026, featuring a 5 mile course plus two kids races for ages 2 to 6 and 7 to 12. Organized by Run the Farm Races and sanctioned by USA Track and Field.

C'mon Armageddon offers 50K, 10 Miler and 5 Miler trail races in Norvin Green State Park, featuring boulder fields, river crossings and steep climbs with skyline views. Awards and GAIA GPS routes make it a rugged, scenic challenge.

Run Like The Wind 5K in Ellenville winds along the base of the Shawangunks and a scenic stretch on the Rail Trail. Finish in Aroma Thyme Bistro's garden with beer, wine and food while supporting food pantries and youth scholarships.

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

Sharpen your trail skills at a three day Spring Training Camp in Oliverea NY. Expert coaching and guided runs on technical Catskill ridgelines include a 13 mile day with 5000 ft of climbing, plus lodging, meals and great camaraderie.

Join the Mine Hill Half Marathon on May 24, 2026, starting and finishing at Mine Hill Distillery in Roxbury, CT. Tackle a scenic hilly road course and celebrate afterward with food, live music and distillery samples.

Join the Forest Park Runners Classic, a scenic 4 mile road and trail out and back in Forest Park, Queens, on Sunday May 24, 2026, featuring chip timing and an overhead finish clock. Pre register for a tech shirt and enjoy post race snacks a..

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

A non competitive National Trails Day run along the D&R Canal Towpath with multiple distance options, bus support to trail access points, per mile charity donations, milestone rewards, and a post run picnic.

Take on ski slopes and mountain trails at Plattekill Mountain Race in Roxbury NY on June 7, 2026. Choose the tough 6.5 mile mountain course with massive elevation gain or the steep, punchy 5k that climbs hard out of the gate.

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

Manitou’s Revenge in Windham, NY on June 20, 2026 is a 53 mile ultramarathon across the Catskills with about 15,000 feet of climbing and rugged, technical trails. Expect long self supported stretches and routes that get harsher after dark.

XTERRA Transcend Trail Run at Dickerson Mine Preserve in Randolph NJ offers lakeside, fast singletrack and scenic loops. Pick 5K, 10K or half marathon and chase qualifying spots for the 2027 XTERRA Trail Run World Championships.

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

Join the XC Summer Series, a friendly weekly cross country 5K on Tuesday nights in Parsippany from April 28 to September 1, 2026. All ages and abilities welcome, walkers included, with chip timing and after race refreshments.

Enjoy a free LVRR Summer Series 5K at Lehigh Parkway on July 1, a friendly, mostly flat cinder trail run for all paces. Part of a five race first Wednesday series May through September, open to ages 10 and up.