Trail Running calendar near Cheshire 2025-2026

NSRF Long Island Turkey Trail Trot 5K is a family-friendly trail run/walk held at Bethpage State Park, Polo Field in Bethpage, NY. The 5K course takes participants through scenic, grassy polo-field starts into winding soft trails with mostly flat terrain and a few small hills, offering a beginner-fr..

Set in Tarrywile Park, Danbury, Connecticut, the Tarrywile Half Marathon offers three distances—10K, Half Marathon, and Marathon—through rugged park trails. The course is renowned for substantial elevation and technical Northeast single-track sections, delivering views of Danbury and the park’s tran..

Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It is the fourth and final race in WTAC’s Fall Trail Race Series, offering two trail distances: 8 miles and 4 miles on Watchaug Pond area trails. Expect a classic, wooded trail course around the pond, with..

Located in Brookhaven State Park, Wading River, NY, the Brookhaven Trail Half Marathon and 5 Mile offer two trail-running distances. The course traverses a mix of Suffolk County woodlands, including single-track, fire roads, sandy sections, and hidden ponds, starting near the park entrance off Willi..

Fall Fling 400, the CT Trailmixers’ ninth annual trail race, takes place at YMCA Camp Sloper in Southington, CT. The event offers two options: Fall Fling 400, where runners complete as many roughly two-mile loops as possible within a 400-minute limit (roughly 28 miles minimum), and the Spring Fling..

The Roxbury Thanksgiving Day Charity Race is a 5K event held annually in Roxbury, Connecticut. Scheduled for Thanksgiving Day, November 27, 2025, the race takes place at the Everett B. Hurlburt Community Park located at 18 Apple Lane.Participants run a 3.1-mile course, offering a community-focused a..

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..

NSRF 50/50 Turkey Trot 5K is an in-person trail run/walk held at Belmont Lake State Park in West Babylon, New York. The event features a 5K trail course around the park’s water-side setting, described as a fun and challenging route. Participants compete not for traditional awards but for a cash raff..

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 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..

Tower Tag Challenge is a trail-running event at Sleeping Giant State Park in Hamden, Connecticut. Runners tackle the Tower Trail, a mostly smooth crushed-gravel carriage road that climbs about 600+ feet in 1.5 miles to the park’s Observation Tower, offering views of the surrounding landscape and, on..

PPTC Endurance Fest in Brooklyn’s Prospect Park offers 50-mile and 50-kilometer ultramarathon options on a looped course of 9 or 15 laps of 3.33 miles. The race begins and ends near the Lincoln Road Entrance and honors NYC’s road-ultra heritage, including Knickerbocker 60k and Metropolitan 50 Mile...

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..

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..

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..

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,..

Run Across CT is a coast-to-coast ultramarathon across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The course covers 123 miles and is offered as Solo 100k or Solo/Relay 200k (3–6 person teams). Runners traverse 25 towns, with about 57 miles on..

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..

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..