Trail Running calendar near Milford 2026-2027

The final Conquer the Trail Race is a 7.5 km run on the flat Croton Aqueduct Trail. This special edition supports Mercy University's Mav Market and celebrates the school's 75th anniversary. The event offers awards, raffles, and free parking..

Run or walk a 5K through the orchards of Brooklyn Cider House. Registration includes a cider glass, donut, and finisher medal. The event is open to all ages and welcomes dogs and strollers.

Run or walk for ospreys at the Lacawac Sanctuary. This event on April 19, 2026 features a scenic 10K trail run and a 5K walk. Proceeds support habitat conservation at the Browning Beaver Meadow Sanctuary.

Event Overview The Squatchywaska Mountainfest is a trail running event with two distances: a 25K (noted as closer to 17 miles) and a 10-mile race. Both courses follow a lollipop format through Minnewaska State Preserve on the Shawangunk Rid..

The Wawayanda Trail Fest offers four distances on a scenic 26+ mile loop in Wawayanda State Park. The course features rhododendron tunnels, marsh bridges, and varied terrain. Crew access and camping are available at the central event site.

A scenic and classic spring run for athletes aged 30+. Choose between the 10K and 5K distances on a mostly flat loop course through woods and around Birchwood Lake in Mountain Lakes. Be prepared for varied surfaces including paths, trails,..

The Leatherman's Loop is a classic 10k trail race held each spring at Ward Pound Ridge Reservation. Entry is secured via a lottery system, with no same-day registration. It's part of a series of trail events including Run the Farm and Raven..

Try the Trail is a youth trail run for ages 4 to 16 at Katonah Memorial Park. Kids can choose between a half-mile or one-mile course on scenic, easy-to-follow trails. It's a family-friendly event focused on outdoor activity.

The XC Summer Series offers weekly Tuesday evening 5K cross country races in Parsippany's Central Park. The thirteen race series welcomes all ages and abilities, with chip timing and post race refreshments. Participants can register for the..

An ultramarathon in Van Cortlandt Park featuring an initial flat lap plus ten cross country loops, stocked aid stations, drop bag access, and finisher awards including a medal, singlet, meal and post race beer.

A Run to Remember in Red Hook NY features 5K and 10K trail races plus a 5K walk on May 2, 2026. Courses run through meadows, forest, orchards and berry patches and cash prizes are awarded.

The first annual Lawrence Hopewell Trail 5K supports a 20-mile community trail. The race course passes by two lakes and the historic Hunt House. A non-competitive one-mile Fun Run is also offered for all paces.

Rock The Ridge is a 50-mile endurance challenge set in the scenic Shawangunk Mountains of the Mohonk Preserve. The event also features a trail marathon and relay options, all while raising funds to support the preserve's conservation and ed..

The Bear Mountain Trail Challenge will take place in Bear Mountain on Saturday 2 May 2026. You can run between 10 and 50 kilometers.

Tackle the steep, technical trails of Breakneck Ridge near Beacon, NY. The course features significant elevation, panoramic vistas, and historic paths. Choose from a 42K or 21K distance on this challenging route.

Green Traill 5K on May 3, 2026 in Easton, PA features a 5K run, a 2 mile walk and a free kids fun run for ages 1 to 10. The volunteer organized event donates all proceeds to Friends of Historic Easton Cemetery.

A weekly cross country series offering thirteen 5K races on Tuesday nights from April to July. The event takes place at Central Park in Parsippany and is open to all ages and abilities. Participants can register for the full series or pay f..

Tackle the steep, rocky trails of Miller Mountain in Tunkhannock, PA. Choose the grueling 25k with four major climbs or the scenic but tough 5-mile option. All finishers get a custom gift and meal, with proceeds supporting local land conser..

This community trail run on Clausland Mountain honors caregivers and supports mental health and sobriety causes. Participants take on a 3.75-mile historic course, receiving a medal in an event focused on gathering, not competition.

The Bruynswick Winery Run for UCSPCA will take place in Gardiner on Saturday 9 May 2026. You can run 6 kilometers.