Trail Running calendar near Highland Lakes 2025-2026

Run the 52nd Jack Bristol Lake Waramaug Ultra in Kent CT on April 26 2026 for scenic, mostly flat loops around the lake with 100K, 50 Miler and 50K options. Expect stocked aid stations, finisher swag and lakeside views to inspire.

Tackle a scenic 10k trail at Leatherman's Loop in Cross River NY on April 26, 2026 for a lively, USATF sanctioned race through Reservation Road. Entry is by lottery with registration opening January 2, 2026 so mark your calendar.

Challenge yourself at VCP50k, a scenic but rugged 50k ultramarathon in the Bronx on May 2, 2026. Ten loops of classic cross country trail bring rocks, roots and rolling climbs with stocked aid stations, a custom finisher singlet and post ra..

Tackle rugged, technical single track with steep climbs and exposed sections at Breakneck Point in Beacon NY, choosing 14.5 mile or 26.4 mile distances with big elevation gain. Entry includes post race food, a Patagonia Cap Cool shirt, and..

Join the 5th annual Green Traill 5K on Sunday, May 3, 2026 at Easton Cemetery for a spirited 5K, a community walk, and a Kids Fun Run for ages 10 and under. Organized entirely by volunteers, the event benefits Friends of Historic Easton Cem..

Blue 2 Blue Challenge is a demanding 50K on May 3, 2026 in New Haven, Connecticut, across rugged blue blazed trails with steep, technical climbs. Entry is by waitlist and requires a recent qualifying trail 50K, so come prepared.

Trails To the Sky at Voorhees State Park features a scenic, looped 50k UTMB Index race and a rolling 10k. Expect big climbs, aid stations, on course support and custom medals for all finishers.

Run The Farm is a scenic 5 miles trail race at Muscoot Farm in Katonah, NY, with kids races and a festive farm market finish. Enjoy trails, local treats, and community spirit in spring and fall editions.

C'mon Armageddon brings technical trail running to Norvin Green Park in West Milford, NJ with 50K, 10 mile and 5 mile routes through boulder fields, river crossings and steep climbs. Expect rugged singletrack and a raw mountain challenge.

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.

Run a scenic half marathon in late May starting and finishing at Mine Hill Distillery in Roxbury. The rolling course on pavement and dirt features steady climbs and fun downhills, and the event is cupless so bring your own bottle.

Challenge yourself at Mohawk Mountain in early June 2026 with timed endurance events from 12 hour to 84 hour and distances up to 152 miles. Race solo or with Trail Buddy or Trail Family teams, tackle night sections and enjoy base support an..

Take on the slopes at the Plattekill Mountain Race in Roxbury NY on June 7, 2026, where ski runs and forest trails deliver steep climbs, fast descents and sweeping views. Choose the 6.5 mile mountain course or the punchy 5k and race for top..

Manitou’s Revenge is a 53 mile ultramarathon in the Catskills across rugged, technical trails and massive climbing. Limited aid, long remote stretches and hand over hand sections make it a grueling but rewarding mountain challenge.

Run lakeside singletrack at Dickerson Mine Preserve on scenic mostly flat trails. Choose 21K half marathon, 10K or 5K, then enjoy Black River Barn with outdoor dining and beer on tap.

Join Pinky's Rock n Rolla, a 4 mile trail race through Forest Park's scenic trails in Richmond Hill, NY. Enjoy rugged natural terrain, medals for all finishers, prizes for top runners, and proceeds benefiting Puppy Kitty NYCity.

Run the scenic Pocono hills at Blue Mountain Ski Area on Spartan Trail with a challenging singletrack 10K. Take in narrow trails and sweeping views, and make it a weekend with Spartan obstacle course races for runners and fans.

Ridge Reaper Trail Runs on August 1, 2026 at Ward Pound Ridge Reservation in Cross River NY serve up wooded singletrack, scenic ridge views and challenging climbs across 25K, 50K and 50M options. Expect rugged runnable trails, aid stations..

Take on the Interstate 17 Trail Run, a 17 mile looped trail race at State Line Lookout with serious elevation and rugged technical terrain. Rocky scrambles, waterfalls and required loop check ins make this a scenic tough challenge.

Tackle technical trails at Stokes State Forest with options from a 5K to a challenging 17 mile loop, plus ruck divisions for 10K. Finishers earn a handcrafted wooden medal and unique swag.