Trail Running calendar near Wading River 2025-2026

Take on rugged Traprock at Penwood State Park in Bloomfield CT on April 18, 2026 with 17K one loop or 50K three loop options. Expect rolling, technical single track and rocky trails; bring your own cup for this cupless, chip timed race.

Join the final Conquer The Trail Race on April 18 in Dobbs Ferry for a scenic 7.5 km on the Croton Aqueduct Trail supporting Mercy University's Mav Market. Mostly flat trail with natural obstacles, raffles and shirts for early registrants.

Join the Lake Mohegan Women’s Trail Race at Lake Mohegan in Fairfield CT for 5K, 10K or a 4 hour loop challenge open to women and non binary runners. Enjoy scenic trails, finisher medals, post race snacks and a welcoming community vibe.

Run the 52nd Jack Bristol Lake Waramaug Ultra Races on April 26, 2026 in Kent CT with 100K, 50 mile and 50K options around scenic Lake Waramaug. Flat rolling loops, four aid stations and finisher swag make this a rewarding spring ultra.

Enjoy a spring 10k trail race in Cross River, NY on April 26, 2026, winding through scenic park trails. Entry is by lottery with registration opening January 2, 2026, perfect for trail runners seeking a well organized challenge.

Join the VCP50k in the Bronx on May 2, 2026. It starts with a flat lap then ten cross country loops with rocks, roots and some climbing. Aid stations, drop bags, medal, singlet, hot meal and beer await finishers.

Take on Breakneck Point on May 3, 2026 in Beacon, NY with a rugged half or full ultramarathon featuring huge elevation and technical single track. Expect steep exposed climbs, aid stations, and a finisher shirt and memento.

Blue 2 Blue Challenge is a rugged 50K through New Haven trails, with about 6350 ft of climbing and technical rocky terrain including a summit at Mt Sanford. Expect a cutoff driven, no frills race for seasoned trail runners.

Run the Mount Archer Trail Race Sunday May 3 2026 in Lyme CT with a scenic 9.2 mile loop or a 3 mile option for runners and walkers. Chip timing, aid stations, and proceeds support Lyme emergency services.

Run a scenic 5 mile trail at Muscoot Farm with kids races for ages 2 to 12 and a family friendly vibe. Finish with Farm Bucks to spend at the Muscoot Farmers Market and optional shirts available by advance order.

Explore trails around Soapstone Mountain and Shenipsit Forest at the Soapstone Mountain Trail Races in Stafford Springs, CT on May 17, 2026. Pick a half marathon or 6K, support local trail stewardship, and register January 1, 2026.

Run a scenic 5K through Blydenburgh County Park in Smithtown on May 23, 2026, with a free Kiddie Dash for kids. Join in person or virtually, enjoy trails and post race refreshments while supporting the Never Stop Running Foundation.

Run the Mine Hill half marathon on 24 May 2026 in Roxbury Connecticut, starting and finishing at Mine Hill Distillery. Enjoy rolling country roads with sweeping farm views, then celebrate at the distillery after party.

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.

The Norbrook Farm Brewery Trail Festival will take place in Colebrook on Saturday 13 June 2026. You can run between 5 and 4 hours.

Run the scenic 15.7 mile Nipmuck South Trail at Mansfield Hollow State Park, following the Nipmuck Trail along the Fenton River through woods, fields and a climb to a cliff. Proceeds benefit Connecticut trail stewardship groups and the Blue..

Run Pinky’s Rock n Rolla on July 11 in Richmond Hill NY: a rugged 4 mile trail through 100 year old pines and Queens longest oak forest. All finishers get medals, top three earn prizes, dogs welcome, and proceeds benefit Puppy Kitty NYCity.

The Soapstone Assault is a rugged 5.5 mile trail race in Somers, CT with six climbs and about 1,500 feet of ascent. Limited to 50 runners, it is a tough course for experienced runners and includes a pre race safety briefing and breakfast.

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.

Interstate 17 is a challenging 17 mile trail run on August 8, 2026 in Closter NJ that traces Hudson River viewpoints. Expect rugged technical singletrack, steep climbs and boulder scrambles across four loops with fully stocked aid stations.