Trail Running calendar near Farmington 2025-2026

Mt. Tom Trail Race takes place in Mt. Tom State Park in Massachusetts, with parking at Bray Lake.The event offers multiple distances: a 25k solo, a 25k two-person relay, a 10k, and a 5k fun run/hike, all on rugged single-track trails within the park. The 25k course features about 3,600 feet of eleva..

The Tackle the Trail - Pomfret, CT will take place in Pomfret on Saturday 18 October 2025. You can run between 10 and 42 kilometers.

Tom Centinaro Memorial "Dam" Race is a 3.5-mile trail run/walk hosted by the Wolcott Lions Club in Wolcott, Connecticut. The race unfolds on the scenic, flat Mill Pond Trail at Woodtick Recreation, 201 Nichols Road. This community event benefits local charities and the Tom Centinaro Lions scholarshi..

The Castle to River Run in Garrison, NY, is a scenic running event held in the historic Hudson Valley, featuring a half marathon and a 5K race, along with a kids fun run. The half marathon course winds through Hudson Highlands State Park, passing the historic Osborn Castle and offering a mix of sing..

The Veeder Tree Farm 5K is a running event held in Earlton, New York, at 1235 High Hill Rd. Scheduled for October 19, 2025, the race offers multiple categories including a 5K, 5K Trail Run, and combinations thereof, with options for students as well. The course features a mix of trail and traditiona..

Bimblers Bluff 50K is an off-road foot race held in southern Connecticut, starting at Guilford Lakes School in Guilford. The 50-kilometer course weaves through interconnected woodland preserves on rolling forest roads and rocky single-track, offering a true test of fitness and mental stamina. Unusua..

FALL Run The Farm is a 5-mile trail race held at Muscoot Farm in Katonah/Somers, New York. The course winds through the scenic farm grounds, showcasing the area’s natural beauty and tying the event to the nearby Muscoot Farmer’s Market vibe. The day also includes Fall Kids Run The Farm for younger p..

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..

Fall Back Into The Trails Series returns to Red Wing Recreation Area in Lagrangeville, NY for its 9th annual edition on November 1-2, 2025. The event offers three races: 100k (10x10k loops with about 1,000 ft of gain per lap), 50k (5x10k loops with about 5,000 ft total gain), and 10k (about 1,000 ft..

Stonington Vineyards hosts the Wine Run Turkey Trot 5k at Stonington Vineyards in Stonington, CT. This timed 5k offers a run or walk on a two-lap cross-country course that begins and ends at the winery, weaving through vineyard lanes with occasional uneven footing. The atmosphere blends fitness with..

8 Hours at the Farm, held in Brookfield, CT, is a Steep Endurance trail running event on a rolling country course at Gurski Farm/Williams Park. The race features an approximately 4-mile loop with single-track and farm trails, plus options for 8-hour, 4-hour, and 4-mile races. The event emphasizes a..

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..

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..

Set in Upton State Forest in Upton, MA, the Upton 10.5K and Half Marathon Trail Race offers two distances: a 10.5K trail run and a 21K half marathon, run as two laps. The course features technical, hilly single-track trails and forest roads, with about 720 feet of elevation gain per lap. Aid station..

The NSRF Long Island Turkey Trail Trot 5K is an annual family-friendly run/walk held at Bethpage State Park in Bethpage, NY. The course starts on a grassy polo field and winds through scenic, mostly flat, beginner-friendly trails with a true cross-country feel. Participants enjoy post-race refreshme..