Trail Running calendar near Stonington 2025-2026

The Pumpkin Pacer 5k at White Barn Farm in Wrentham, Massachusetts, is a scenic trail run/walk/hike held annually in late October. This off-road 5K course features dirt and gravel paths with natural terrain including rocks, roots, and elevation changes, offering a fun challenge for all ages and skil..

The Powisset Farm Trail Run - Fall is a popular trail running event held at Powisset Farm in Dover, Massachusetts. Scheduled for October 26, 2025, it offers four race distances: 8.3, 5.6, 3.1, and 1.5 miles, traversing scenic trails through Powisset Farm and the neighboring Noanet Woodlands. The rac..

8 Hours at the Farm is a trail running event held at Gurski Farm/Williams Park in Brookfield, Connecticut. The race features a rolling country course with an approximately 4-mile loop that includes single track and farm trails, offering a scenic and community-focused atmosphere. Participants can cho..

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..

The Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It features two trail running events: an 8-mile and a 4-mile course, both winding around the scenic Watchaug Pond. This race is part of the WTAC Fall Trail Race Series, offering a 10% discount for parti..

The Baystate Dirty Dog Trail Run-Ruck-Walk 5k is a rugged outdoor event held in Berkley, Massachusetts, honoring military personnel, first responders, and their K-9 partners. Participants can run, ruck with weighted packs, or walk a challenging 5k trail through scenic natural landscapes, often muddy..

The Fall Fling 400 is an annual trail running event hosted by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut. It features two main races: a 400-minute timed trail race where participants complete as many loops as possible on a roughly two-mile course with rolling hills and varied..

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 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 Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5K 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 experience.P..

The TARCtic Frozen Yeti is a winter trail running event hosted by the Trail Animals Running Club at Hale Reservation in Westwood, Massachusetts. It offers two distance options: a 15-mile race and a challenging 30-hour endurance race. The course features three roughly 5-mile loops marked with colored..

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 with over 3,000 feet of vertical gain and a 50K option for runners who complete two l..

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..

The TARC Spring Classic is a trail running event held annually at Jericho Town Forest in Weston, Massachusetts. Offering 10K, Half Marathon, Marathon, and 50K distances, the course features a relatively flat, smooth 10K loop with twisting trails suitable for all skill levels. Runners complete multip..

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..