Trail Running calendar near West Hartford 2025-2026

The Grills Trail Run, hosted by the Westerly Track & Athletic Club, takes place at Grills Preserve in Westerly, Rhode Island. Scheduled for October 25, 2025, it features two race distances: a 10-mile and a 10K. Both courses start and finish at Grills Preserve, showcasing scenic trails with about 80%..

Book It for Books 5k & 10k is a charity running event at Lake Accotink Park in Springfield, VA, benefiting Reading is Fundamental of Northern Virginia (RIF NOVA). The weekend features a 1-mile fun run, a 5k trail out-and-back on the lake’s south side, and a 10k course that runs out-and-back on the n..

Pumpkin Pacer 5k @ White Barn Farm is a 5K off-road trail run/walk held at White Barn Farm, 431 South Street, Wrentham, MA 02093. It’s the final race in the Farm To Trail 5K Series and is open to all ages and abilities. The course weaves through scenic conservation land and farm property, featuring..

RACE FOR THE GREENWAY 5K RUN / WALK takes place at Hallock State Park in Riverhead, NY. The mostly flat off-road 5K course weaves through parkland with views of beaches, vineyards, ponds, and forests, featuring loose gravel and grass underfoot. Runners and walkers of all abilities are welcome.After..

The Fall Back Into The Trails Series will take place in Lagrangeville on Saturday 1 November 2025. You can run between 10 and 100 kilometers.

Stonington Vineyards Wine Run Turkey Trot 5k is a timed 5k run/walk held at Stonington Vineyards in Stonington, Connecticut. The two-lap cross-country course begins and ends at the winery, winding through vineyard lanes with some uneven footing, suitable for runners and walkers alike. The Thanksgivi..

8 Hours at the Farm is a trail running event by Steep Endurance in Brookfield, Connecticut, on the rolling grounds of Gurski Farm/Williams Park. The race features approximately a 4-mile loop weaving single-track and farm trails, delivering a rolling, not-too-technical course and a supportive trail-r..

Set in Sleepy Hollow, New York, the Pocantico Hills Marathon offers two distances: a full marathon and a half marathon run through Rockefeller State Park Preserve. The courses are single loop, rolling and hilly, with scenic views of the Hudson River and the Palisades. Runners pass past fields, stone..

Race for DFL is a last-runner-standing backyard ultra held at Kenty’s Farm in Winchendon, Massachusetts. The event uses a single lap of about 4.17 miles, with a course mixture of grassy field, forest trail, crushed gravel bike path, and a dirt road, totaling around 150 feet of elevation gain per lap..

The Upton Half Marathon Trail Race, held in Upton State Forest, Massachusetts, offers a challenging and scenic trail running experience. Participants can choose between a 10.5K or a half marathon distance, with the half marathon consisting of two laps of a 6.5-mile course featuring technical, hilly..

Raven Rocks Run is a challenging 10k trail race held at Ward Pound Ridge Reservation in Cross River, New York. The route climbs to the park’s highest points, including Raven Rocks Overlook and the Fire Tower Summit, before a mostly downhill finish along rugged ridgelines, rocky climbs, meadows, and..

The Centerville Bank Thompson Turkey Trot is an annual event held at the West Thompson Dam Overlook Shelter in Thompson, Connecticut. It features a 5K timed trail run, a 3K untimed walk called the "Wobble" where dogs on leashes are welcome, and a free kids' fun run for children 12 and under. The eve..

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 Marathon, Half Marathon, and 10K trail distances. The course is renowned for its toughness, with close to 3,000 feet of elevation and substantial Northeast single-track, featuring rocky, rooty, and hilly terrain. The rou..

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..

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 held at Sleeping Giant State Park in Hamden, Connecticut. The course follows the Tower Trail, a crushed-gravel carriage road that climbs about 600 feet in 1.5 miles to the Observation Tower, offering sweeping park views and, on clear days, Long Island Sound. Each Tower Tag att..