Trail Running calendar near East Islip 2025-2026

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Join the John Jay Community Trail Race in Cross River, NY for a scenic, hilly trail 5k, a 4k community walk and a fun Kids Jay Dash. Enjoy wooded trails, a finish on the contest field and community spirit with shirts for early registrants.

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.

Wawayanda Trail Fest in Hewitt New Jersey offers distances from a half marathon to a 100K through rhododendron tunnels, marsh bridges and winding single track. Aid stations and on site camping make for a friendly, challenging trail weekend.

XTERRA New Jersey at Wawayanda State Park is a weekend off road race festival with trail runs, mountain and gravel biking, triathlons and a paddle triathlon. Camp lakeside and soak up live beach music between races.

Celebrate women and non binary runners at the Lake Mohegan Women’s Trail Race on April 25, 2026 with scenic trails around the lake. Pick a 5K, 10K or a 4 hour loop to challenge yourself and earn a finisher medal.

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..

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 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.

Tackle the Mine Hill Half Marathon, a scenic road race that climbs hard in the first half then rewards you with a fast mostly downhill return to Mine Hill Distillery in Roxbury. Finishers get a medal and a lively post race celebration.

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..

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 Ridge Reaper at Ward Pound Ridge Reservation with 25K, 50K, and 50M courses through technical singletrack and scenic carriage roads. Big climbs, ridge views, and a cupless format so carry your own hydration.

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 a scenic 5K through Oswegatchie Hills Nature Preserve, winding past Clark Pond on root and rock strewn trails; hikers welcome. This fourth annual run benefits preserve maintenance and finishes with local pub awards and camaraderie.