Trail Running calendar near Wading River 2025-2026

SRC Presents: A Backyard Ultra takes place at Blydenburgh County Park in Hauppauge, NY on December 13–14, 2025. The event features two races: A Backyard Ultra, a true ultramarathon where runners must complete a 4.167-mile loop within an hour, repeatedly until only one runner remains; and The 1 Lappe..

Frosty Fat Sass is a family-friendly trail party in West Orange, New Jersey, held at the Turtleback Rock Picnic Area in the South Mountain Reservation. It offers a 5K loop and timed options of 3 hours or 6 hours, plus a new Rucking division with lightweight (15 lb) and heavyweight (30 lb) packs. The..

Squatchy Onesiefest 5K is a Sassquad Trail Running trail party at Ramapo Valley County Reservation in Mahwah, NJ. The 5K is run as a 1.6-mile lollipop loop repeated twice, starting and finishing at the NYNJTC Headquarters; park in the reservation lot. The route is very mellow: a flat gravel/dirt tra..

The Febapple Frozen event is a trail running race held in South Mountain Reservation, Maplewood, New Jersey. Scheduled for February 21, 2026, it offers multiple distance options including a 50-mile, 50-kilometer, 20-mile, and 10-mile race. All distances are based on a roughly 10-mile loop course sta..

Squatchapple is a West Orange, NJ trail race held in the South Mountain Reservation, starting and finishing at the Tulip Springs Trailhead on Cherry Lane. The Sassquad Trail Running event offers 11M, 20M, 50K, and 50M options built from three loops: 4M Turtleback, 5.5M Locust Grove, and 7M Mayapple...

Livingston Oval Ultra takes place in Livingston, New Jersey, at the public Livingston Oval on Robert Harp Drive. On March 7, 2026, the 3rd annual event offers 12-hour, 6-hour, 3-hour and 1-hour options, with runners looping the Oval. The fast, flat course is USATF-certified (as of Aug 1, 2023) and i..

Located in Union, Connecticut, the Northern Nipmuck Trail Race is a 16-mile ultramarathon staged just outside Bigelow Hollow State Park. The course runs south on the Nipmuck Trail through the Yale-Myers Forest, crosses Barlow Mill Rd at mile 4, then reaches a turnaround at Boston Hollow before retra..

Sleeping Giant Trail Runs, hosted by Steep Endurance at Sleeping Giant State Park in Hamden, CT, offers challenging 25K and 50K trail races through Connecticut’s iconic park. The 25K loop features more than 3,000 feet of vertical gain across rocky and rolling singletrack via Yellow, Chestnut, White,..

Big Bear Squatch North is a challenging trail running event held at Harriman State Park in Bear Mountain, New York. Featuring a half marathon and 10K races, including a new rucking division with lightweight (15 lbs) and heavyweight (30 lbs) pack categories, the event showcases rugged, technical moun..

The Spring SOMO Timed Trail Races take place at South Mountain Reservation in South Orange, New Jersey. This event features a looped trail course of 1.88 miles (just over 3K) that includes single track, pavement, and fire road sections. Runners can choose from multiple race options: 1 loop (3K), 2 l..

John Jay Community Trail Race is a community running event in Cross River, New York, on the John Jay Community Cross Country Trail. The event features a 5k Trail Race, a 4k Jay Walk, and a Kids Jay Dash, a 200-meter race. The 5k winds through wooded, rolling terrain starting on the John Jay Campus l..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high demand, entry is determined by a lottery system.The registrati..

Jack Bristol Lake Waramaug Ultra Races run around Lake Waramaug in Kent, Connecticut, offering 100K, 50M, and 50K. One of the oldest ultras in the United States, it marks its 52nd anniversary in 2026 as part of the Mount to Coast 100K Series. The rolling, mostly flat course uses paved roads around t..

The VCP50k is an ultramarathon held in Bronx, New York, founded in 2023 and designed to accommodate both novice and experienced runners. The race features a challenging yet accessible course consisting of ten loops on the classic Tortoise and Hare cross country trail, plus an initial lap on flat ter..

Breakneck Point Trail Runs, hosted by Red Newt Racing, take place at University Settlement Camp in Beacon, NY. The event offers two challenging distances: a half marathon of approximately 14.5 miles with 4,800 feet of elevation gain, and a full marathon of about 26.4 miles with 9,000 feet of gain. T..

Run The Farm is a trail-running event held at Muscoot Farm in Katonah/Somers, NY. The centerpiece is a 5-mile trail race through farm fields and woodlands, complemented by two Kids Run The Farm events for younger runners. The course highlights Muscoot’s rural scenery and woodland trails, creating a..

The Nipmuck South Trail Race is a 15.7-mile out-and-back trail run held in Mansfield, Connecticut, starting at Mansfield Hollow State Park. The course follows the scenic Nipmuck Trail alongside the Fenton River, featuring varied terrain including small bridge crossings, a climb to a 50-foot cliff, f..

Pinky’s Rock n Rolla is a unique 4-mile trail race held in Richmond Hill, New York, offering runners an authentic trail running experience on natural hiking trails rather than typical bridle paths or gravel roads. The course, located in Forest Park, features naturally carved terrain shaped by glacia..