Trail Running calendar near Tolland 2026-2027

The Tarrywile Half Marathon challenges runners on technical, hilly trails in Connecticut's Tarrywile Park. With three distances available, the cupless event emphasizes trail respect and community. All finishers earn a unique medal.

A trail race at Burlingame State Park in Charlestown on November 15, 2026, offering 4-mile and 8-mile courses around Watchaug Pond. It is the first race in the WTAC fall trail series with multi-race registration discounts.

Experience a magical 13.1 mile trail race through the rolling hills of Roosevelt Forest. Complete eight loops of a wooded course while supporting a children's book drive in this unique costume friendly event.

Test your endurance at YMCA Camp Sloper with a 400 minute timed challenge or a 4 mile trail race. Explore rolling wooded trails in Southington while supporting local charities and youth running programs.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A Thanksgiving morning trail run supporting endometriosis research. Choose a run or walk on the 3.5-mile Mill Pond Trail, followed by complimentary yoga. All participants get a finisher medal and swag bag.

TARC Winter Classic in Stoneham offers 8, 32 and 40 mile trail races on the white blazed Skyline Trail with rugged roots, rocks, frequent climbs and Boston skyline views. Expect technical trails, minimal markings and a festive finish.

The Tower Tag Challenge is a timed trail run in Connecticut's Sleeping Giant State Park. Runners complete 3.4-mile laps up and down the scenic Tower Trail within an 8-hour or 4-hour window. The event features awards, post-race refreshments,..

Experience a unique cross country tradition at the Mount Hood Golf Club with a hilly 3.5 mile run or a festive 2 mile walk. Compete for nutcracker awards and enjoy a post race pasta lunch for a good cause.

Experience an exclusive trail run through the scenic Roosevelt Forest in Stratford. This 5K event features a natural off-road course limited to a small group of participants and includes custom finisher medallions.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.