Trail Running calendar near Farmington 2025-2026

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..

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..

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..

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..

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..

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..

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..

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..

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..

The TARC Wapack and Back is a challenging trail running event held annually in Ashburnham, Massachusetts, along the scenic Wapack Trail. Offering three distance options—21.5 miles, 43 miles, and 50 miles—the race features rugged terrain with rocky ledges, boulder fields, granite slabs, and technical..