Trail Running calendar near Wading River 2025-2026

Febapple Frozen invites you to a winter trail challenge at South Mountain Reservation on Feb 21, 2026, with 10 mile loops and distances from 10 miles to 50 miles. Aid stations, official timing, event swag and awards for top finishers add ra..

Squatchapple in West Orange, NJ on March 7, 2026 offers 11, 20, 50K and 50 mile trail races over three scenic loops in South Mountain. Expect rugged singletrack, big climbs, handcrafted wood finisher medals and a fun trail festival vibe.

Take on the Livingston Oval Ultra in Livingston NJ on March 7, 2026 with 1, 3, 6 or new 12 hour timed lap options on a fast, flat USATF certified course. Friendly aid stations, custom awards and a loop made for high mileage await.

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Run under the pines at the Enchanted Forest Ultra Run in Roosevelt Forest, Stratford CT, offering a 6 hour or 50K timed trail challenge on rugged trails. Only 50 entries, costumes welcome, with pizza, aid stations and medals.

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

Take on rugged singletrack, a steep headwall scramble and 3,000 feet of climbing at Sleeping Giant Trail Runs, with 25K and 50K options. At Sleeping Giant State Park in Hamden CT on March 29, proceeds benefit the park and finishers get meda..

Run rugged trails at Big Bear Squatch North in Harriman State Park on April 4, 2026 with half marathon, 10K and ruck divisions. Expect steep climbs, scrambling terrain and sweeping Hudson Valley and NYC skyline views.

Join the Spring SOMO Timed Trail Races at South Mountain for looped racing on a scenic 1.88 mile course of single track, pavement and fire road. Run a 3K or 6K or take on the 1 hour, 3 hour or 6 hour timed challenge.

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.

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..

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.

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.

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.

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.