Trail Running calendar near Stamford 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..

On May 3 2026 Breakneck Point Trail Runs in Beacon NY offers a half at about 14.5 miles and a full at about 26.5 miles on rugged, technical trails with steep climbs and exposed sections. Expect big elevation, scenic views, aid stations, 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.

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.

Run Like The Wind 5K in Ellenville offers a scenic course along the Shawangunk Mountains and the newly resurfaced Rail Trail. Finish at Aroma Thyme Bistro for garden drinks and food while supporting local food pantries and youth scholarship..

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.

IronHike Series Spring 26 takes place June 4 to 7 at Mohawk Mountain, CT, with solo and team endurance options from 15 to 152 miles. This non competitive FlexRelay invites crews to self manage pacing, rest and night trekking.

Join Norbrook Farm Brewery Trail Festival on June 13, 2026 in Colebrook CT for a day of trail runs and mountain bike races on scenic farm trails. Multiple distances, awards and a free beer for those 21 plus create a festive finish.

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 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.

Run the Shawangunk Ridge Trail in Rosendale NY on Sep 12, 2026. Choose 70 mile, 30 mile or half marathon routes through rocky ridgelines, waterfalls and cliffs in a self supported backcountry 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.

Tackle technical single track and big climbs at the Macedonia Trail Race in Kent, Connecticut. Choose 12K, 25K, or 50K loops with Cobble Mountain views and rugged trails for a rewarding, scenic challenge.