Trail Running calendar near Fairfield 2025-2026

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 the Morris County Empanada Trail at Central Park in late March, choose a scenic 5K or 10K over mixed terrain and hills. Finishers get a long sleeve shirt, medal and an empanada with vegetarian options.

Challenge yourself on Sleeping Giant Trail Runs at Sleeping Giant State Park with 25K and 50K options. Expect rugged singletrack, a steep 500 foot climb, scenic tower views and over 3,000 feet of vertical gain per 25K loop.

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.

Find your pace at the Spring SOMO Timed Trail Races in April at South Mountain Reservation, NJ, with options from a single 3K loop to 6 Hour timed runs. Enjoy a scenic 1.88 mile loop of single track, pavement and fire road.

Join the John Jay Community Trail Race on April 12, 2026 in Cross River NY for a hilly 5k through wooded trails, a 4k community walk and a 200 m Kids Jay Dash on the track. First preregistered entries earn event shirts.

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.

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.

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.

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.

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.

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 a looped, lit course at the Sussex County Fairgrounds during a weeklong festival offering distances from marathon and 50K to multi hour timed events. Enjoy aid stations, camping and showers plus a live lap display and buckle awards.