Trail Running calendar near Guilford 2025-2026

The 2025 Never Stop Running Foundation Leftover Turkey Trot 5K is a festive run/walk event held at Bethpage State Park in Bethpage, New York. Participants enjoy a scenic course starting on a grassy polo field and winding through mostly flat, beginner-friendly soft trails with a true cross-country fe..

Rob's Trail Run Edition is a trail running event held in Woodbury, New York, at Stillwell Woods Preserve. Scheduled for November 30, 2025, the event features two main races: a 5K Adult Trail Run for participants aged 19 and older, and a 5K High School or Youth Trail Run for those 18 and under. The c..

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 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 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 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...

Run Across CT is an ultramarathon event featuring a 123-mile point-to-point course across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The route traverses 25 towns and combines approximately 57 miles of well-maintained trails with scenic backroa..

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 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..

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..

The Pinky’s Rock n Rolla will take place in Richmond Hill on Saturday 11 July 2026. You can run 4 miles.