Trail Running calendar near Milford 2026-2027

Trail race at Tarrywile Park in Danbury, CT, offering Marathon, Half Marathon and 10K on technical, hilly single-track trails with finisher medals, podium awards and a $600 half-marathon time bonus.

The FEAR Trail Fest is a 5-mile trail race on the scenic Yellow Trail in New Jersey's Lewis Morris Park. With a runnable mix of rocks, roots, and climbs, it welcomes everyone from first-timers to veterans. The event focuses on sustainabilit..

Celebrate the holiday at the Inwood Hill Turkey Trot 5K Run and Walk. This event offers a scenic course through Inwood Hill for participants of all abilities to enjoy a morning of fitness and community.

An annual Roxbury Road Runners charity race held on Thanksgiving Day, with proceeds supporting the Roxbury Scholarship Foundation and the Roxbury Ambulance Association. Results for the race are published as part of the club series.

FSX Black Friday 100 is a one-day ride and run on the Fifth Street Cross course in Emmaus, offering distances from 10k to 100 miles plus relay and mixed run and ride options. Entry is $25 plus a 6-pack or a $20 prize pot contribution.

A looped trail party at South Mountain Reservation in West Orange NJ offering 5K, 10K, 25K, 50K and a kids 1 mile on a mixed carriage road and singletrack course with onsite aid and a charity partnership.

Experience a 5K trail race through the scenic Stillwell Woods Preserve in Woodbury. This event honors the memory of Rob Lauterborn and supports the Center for Developmental Disabilities.

A looped trail race at Holmdel Park with a 50K (ish) and a Halfish option on ~4.65 mile laps, varied trail terrain, RFID lap timing, and an 8 hour cutoff. Proceeds support MissionCleanWater.

Timed-lap ultrarun at the Livingston Oval where runners log laps for one, three, six, or twelve hours on a USATF-certified flat course; aid station support, tech race hats, and a 2027 finisher medal are included.

Trail runs in Middlesex County near Edison with a secret start, offered distances around 2 and 5 miles, a post-run social, and a requested canned food donation; registration fees are listed and volunteers receive event items.

A social trail event in Edison with a 5 mile trail run and a shorter group run, marked trails, potential trail hazards, volunteer perks, a post-run social for those over 21, and a canned food donation request.