Trail Running calendar near Milford 2025-2026

Hit the rolling, rugged singletrack at Rockland Rad Run Sunday April 12 2026 at Forever Farm in Mertztown PA, a trail running festival for all abilities. Choose a marathon, half, 10k or 5k then relax with postrace food and a free drink.

Tackle wooded trails at the Farm & Forest All Terrain 5K and Hog Wild Kids Fun Run in Stamford, CT on April 12, 2026. Family friendly and community focused, this race raises funds for the Stamford Museum and Nature Center.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry for a scenic 7.5 km on the Croton Aqueduct Trail supporting Mercy University's Mav Market. Mostly flat trail with natural obstacles, raffles and shirts for early registrants.

Celebrate spring at the Brooklyn Cider House Spiked Apple 5K on April 19 in New Paltz, a scenic two lap run through vineyards and orchards. Enjoy a cider pour, fresh donut, finisher medal and commemorative shirt.

Join the 10K Run for the Osprey at Lacawac Sanctuary on Sunday April 19 2026, with a scenic 10K trail run and a family friendly 5K walk supporting sanctuary conservation. Expect wooded trails, osprey sightings, and awards for top finishers.

Squatchywaska Mountainfest in Ellenville NY on April 25, 2026 serves up technical singletrack on the Shawangunk Ridge with 25K and 10 mile options, big climbs and sweeping Catskill views. This rugged trail event also supports protection of..

Wawayanda Trail Fest brings spring trail running to Wawayanda State Park NJ with rhododendron tunnels, marsh bridges and scenic single track. Distances include a new 100K plus 50 mile, 50K and half marathon, with aid stations and on site ca..

XTERRA New Jersey brings trail runs, mountain and gravel bike races, triathlon, paddle triathlon and duathlon to scenic Wawayanda State Park on April 25 and 26, 2026. Expect rugged courses, lake swims and festival vibes for all levels.

Run the 52nd Jack Bristol Lake Waramaug Ultra Races on April 26, 2026 in Kent CT with 100K, 50 mile and 50K options around scenic Lake Waramaug. Flat rolling loops, four aid stations and finisher swag make this a rewarding spring ultra.

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Join the VCP50k in the Bronx on May 2, 2026. It starts with a flat lap then ten cross country loops with rocks, roots and some climbing. Aid stations, drop bags, medal, singlet, hot meal and beer await finishers.

Join A Run to Remember on May 2 in Red Hook and run or walk scenic farm trails through meadows, orchards, and woods at Greig Farm. Honor loved ones, celebrate community spirit, and vie for cash prizes in the 5K and 10K races.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Run or walk the fifth annual Green Traill 5K in Easton on May 3, 2026 at Easton Cemetery, a volunteer run raising funds for Friends of Historic Easton Cemetery. Enjoy a timed 5K, a 2 mile walk, kids fun run and post race refreshments.

Test your legs on rugged trails and sweeping Susquehanna views at the Miller Mountain Trail Challenge in Tunkhannock, PA, with 25K run or hike and 5 Mile options featuring steep climbs and rocky descents. Finishers get custom swag, a finish..

Trails To the Sky at Voorhees State Park invites runners to tackle a scenic, hilly trail course with a UTMB index 50k and a shorter 10k option. Expect rugged singletrack, observatory views, friendly aid stations, and custom finisher medals.

Run a scenic 5 mile trail at Muscoot Farm with kids races for ages 2 to 12 and a family friendly vibe. Finish with Farm Bucks to spend at the Muscoot Farmers Market and optional shirts available by advance order.

C'mon Armageddon is a rugged trail race in Norvin Green State Park NJ offering 50K, 10M and 5M routes over boulder fields, river crossings and rocky peaks with skyline views. Big climbs and technical terrain make it a true test.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

Recharge your trail legs with a small group spring camp in Oliverea, NY, in the Catskills. Tackle technical scrambles and big climbs while getting on trail coaching and mental performance work to sharpen your skills and confidence.