Trail Running calendar near Milford 2026-2027

A 53-mile Catskills ultramarathon with about 15,000 feet of climb, technical trail sections, nine aid stations and a 23-hour cutoff. The point-to-point route starts near Windham and finishes in downtown Phoenicia.

XTERRA Transcend Trail Run on June 20, 2026 at Dickerson Mine Preserve in Randolph New Jersey offers 21K, 10K and 5K trail races on lakeside singletrack with limited event mementos and post race food and drinks.

Operation WOODSTOCK on June 20, 2026 in Elka Park, NY is a 14.5 mile load bearing event with 5,210 ft elevation gain and a 20 lb dry pack. Entry is listed at $105 plus $7.35 tax.

The Jade's Belmont Plateau 5K will take place in New York on Saturday 20 June 2026. You can run 5 kilometers.

A trail and dirt-road event near Tunkhannock, PA offering a half marathon (two laps of the 10K), a 10K, 5K run/walk and a 2 mile fun walk on varied terrain with substantial climbing and multiple aid stations.

An all-day looped trail event at Tyler State Park on June 20, 2026, with alternating-direction 5 mile trail and paved loops over an 11 hour window. Entry is $25 and Bucks County Road Runners members may be eligible for free or reduced entry..

Three one mile races on track, grass and road at a single venue in Clark, New Jersey. Each mile is timed separately and cumulative times decide overall scoring, with two hours allotted to complete all three.

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..

An 8.6 mile trail run at Minnewaska State Park Preserve on June 24, 2026, over unpaved carriage paths with chip timing and commemorative towels for all finishers.

An obstacle course backyard ultra where athletes run an approximately 3 miles loop every hour until one remains. Solo and relay formats are available, with a 50 mile solo option and team relays for groups of three to six.

Test your endurance on a 2 mile paved loop at the Rodale Park 12 Hour Challenge. Cycle, run, or walk to support the development of the September 11th National Memorial Trail.

A 3.1 miles moonlight trail run at Lakeside Park in Pawling, NY with varied terrain, glow markers, required personal light, post run towel and a handmade finisher medal. Proceeds support the Pawling Recreation Department.

Experience a unique trail race through the Westmoreland Sanctuary where you choose your own path at the fork. Start and finish at Fox Lane High School for a memorable 5k adventure in Bedford.

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..

A free 5K at Lehigh Parkway on July 1, 2026, part of a summer series held the first Wednesday each month May through September. The measured, mostly flat cinder course has a 60 minute time limit and a minimum age of 10 years.

A trail event at Red Wing Recreation Area on July 5, 2026, offering 15K, 30K, and 60K options across a 15k loop with mixed terrain, on-course aid stations, post-race food, and awards for top finishers.

Part of the Shawangunk Runners summer series, this week features a 4.7 mile Undercliff Overcliff loop plus kid races, held at Trapps Bridge with parking at Mohonk Preserve West Trapps and no registration fee.

A mid summer cross country series at RVA Fields in Boonton, NJ, with four Monday 5K races in July and August plus a separate 6K and a relay. Entry is offered for individual races and for the full series.

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..

A midweek trail event in South Mountain Reservation offering a kids mile and a 5K with a central event hub featuring a DJ, vendors, food trucks, a 100 minute course cutoff, and participant tees.