Trail Running calendar near Litchfield 2025-2026

Run the John Jay Community Trail Race in Cross River on Sunday April 12, 2026 for a scenic 5k through wooded, hilly school trails and a family friendly 4k walk. Kids can sprint the 200 m Jay Dash on the track and celebrate a student built c..

Take on the rugged Traprock trail at Penwood State Park with a single 17K loop or three loops for the 50K for a true trail challenge. Expect rocky, technical single track, rolling terrain and great forest views.

Run the Shore2Shore on April 18, 2026 in East Islip, NY, a scenic point to point along the Long Island Greenbelt Trail from Sunken Meadow to Heckscher State Park. Choose 25K or 50K with well stocked aid stations and finish swag.

Tackle rugged singletrack, cliffs and glacial ledges on the Shawangunk Ridge in this scenic mountain trail race offering 25K and 10 mile courses. Proceeds support Run Wild's campaign to protect Verkeerder Kill Falls.

Celebrate trail running at the Lake Mohegan Women’s Trail Race, welcoming women and non binary runners to scenic loops in Fairfield, CT. Pick a 5K, 10K or a 4 hour loop challenge and finish with medals, podium prizes and great community vib..

Take on Wawayanda Trail Fest at Wawayanda State Park, offering distances from half marathon to 100K. Run through rhododendron tunnels, marsh bridges and single track on a scenic 26 mile loop with friendly aid stations.

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.

Leatherman's Loop is a scenic spring trail 10k in Cross River, NY, welcoming runners of all levels to enjoy winding park trails on April 26, 2026. Entry is by lottery and the fee includes park admission.

XTERRA New Jersey is an off-road multisport event held at the scenic Wawayanda State Park, featuring over 40 miles of trails and a clear lake. Part of the XTERRA World Tour, it offers a variety of races including trail runs (5K to 42K), gra..

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..

Run Breakneck Point in Beacon NY on May 3, 2026 with 14.5 mile and 26.5 mile options over technical trails and serious climbing for a rugged spring challenge. Entry includes post race food, a Patagonia Cap Cool shirt, and a finisher medal.

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

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.

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

Take on Ragged Mountain near Berlin CT in a last person standing race. Run a 3.11 mile loop each hour and keep finishing within the hour until only one runner completes a loop and wins.

Run the Forgotten Forest 9 hour Ultra at Roosevelt Forest in Stratford CT, a timed trail on a scenic 2.2 mile loop with roots, rocks and rolling climbs. Limited to 50 runners for an intimate, rugged day on the trails.

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.

Run The Farm is a scenic 5 mile trail race at Muscoot Farm with fun kids races for younger runners. Finishers receive Farm Bucks to spend at the Muscoot farmers market and event shirts are available while sizes last.

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.

Take on the scenic Mine Hill Half Marathon on May 25 in Roxbury, CT, starting and finishing at Mine Hill Distillery. Enjoy a challenging climb, a fast downhill second half, a finisher medal and post race food and drinks.