Trail Running calendar near Rocky Point 2025-2026

The Never Stop Running Foundation 50/50 Turkey Trot 5K is a trail run held at Belmont Lake State Park in West Babylon, NY. This fun and challenging 5K event emphasizes community and excitement over competition, offering no traditional awards or swag but a unique raffle where 50% of net proceeds are..

The Santa's Summit 10k is a scenic and challenging trail run held at Bull Run Marina in Clifton, Virginia. The course follows the Bull Run Occoquan Trail, featuring hilly terrain with a mix of out-and-back and one-way sections. Participants can also choose a 5k distance or a virtual race option.Runn..

The Tower Tag Challenge is a trail running event held at Sleeping Giant State Park in Hamden, Connecticut, known for its scenic views and historic Observation Tower. Participants run repeated loops of the Tower Trail, a 3.3 to 3.4-mile out-and-back course that ascends over 600 feet along a smooth ca..

The PPTC Endurance Fest is an ultramarathon event held in Brooklyn, NY, featuring 50-mile and 50-kilometer race options. Taking place in Prospect Park, the course consists of multiple 3.33-mile loops—9 loops for the 30-mile race and 15 loops for the 50-mile race—starting and finishing near the Linco..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5-kilometer race offers participants a chance to escape the roads and enjoy a scenic course through nature. Runners, joggers, hikers, and walkers are all welcome, with a requirement of some trail exp..

The Holmdel Classic is a challenging end-of-year trail race held in Holmdel Park, Monmouth County, New Jersey. Featuring a 4.65-mile loop with 584 feet of elevation gain, the course covers diverse terrain including grass, dirt, rocks, roots, gravel, pavement, and varied inclines. Participants can ch..

The Frosty Fat Sass is an annual trail running and hiking event held at South Mountain Reservation in West Orange, New Jersey. Scheduled for January 31, 2026, this 9th edition offers participants options to run or hike a 5K loop, or join timed 3-hour and 6-hour challenges, including a new rucking di..

The Squatchy Onesie Fest 5K is a fun and unique trail running event held at Ramapo Valley County Reservation in Mahwah, New Jersey. Participants complete a flat, scenic 1.6-mile "lollipop" loop around Scarlet Oak Pond twice to finish the 5K. The course features mostly wide gravel and dirt trails wit..

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..

The Livingston Oval Ultra, held in Livingston, New Jersey, is a timed running event featuring 1-hour, 3-hour, 6-hour, and a new 12-hour race distance for 2026. Participants run laps around a USATF-certified, fast, and flat oval course, aiming to cover as much distance as possible within their chosen..

Squatchapple is a popular trail running event held at South Mountain Reservation in West Orange, NJ, offering distances of 11 miles, 20 miles, 50K, and 50 miles. The race features a challenging course composed of three loops—4, 5.5, and 7 miles—with varied terrain including carriage roads, singletra..

The Sleeping Giant Trail Runs, held at Sleeping Giant State Park in Hamden, Connecticut, is a challenging trail running event known as one of the toughest in the Northeast. The race offers two distances: a 25K loop featuring over 3,000 feet of vertical gain, and a 50K option consisting of two loops...

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..

The John Jay Community Trail Race, held in Cross River, NY, is a competitive 5k run on the newly developed John Jay Community Cross Country Trail. The course begins on the lower fields of the John Jay Campus, quickly entering challenging, hilly wooded trails near the middle and high schools, and fin..

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..

The Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event celebrating its 52nd anniversary in 2026. It features three race distances: 100K, 50 miles, and 50K, all conducted on primarily flat, rolling loops around scenic Lake Waramaug on paved roads. The..

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 popular trail running event held at Muscoot Farm in Katonah/Somers, New York. The race series features a 5-mile trail run along scenic paths showcasing the natural beauty of the working farm and surrounding parkland. The event includes two kids' trail races tailored for different a..