Trail Running calendar near Tolland 2026-2027

A weekend trail event at Red Wing Recreation Area in Lagrangeville, NY offering 10K, 50K and 100K loop races with continuous aid, finisher medals, and UTMB Index designation for the 50K and 100K.

Timed trail event at Gurski Farm in Brookfield CT featuring continuous 4 mile loops for 8 hour and 4 hour runners plus new 5K and 5K Canicross options. Post race food and beverages are provided.

A trail 10k at Ward Pound Ridge Reservation paired with a November virtual 100k challenge that rewards finishers with a custom engraved woodallion; the race uses rocky ridgeline trails and includes an on-course water stop near the fire towe..

A technical trail event at Tarrywile Park in Danbury offering 10K, half marathon and marathon distances with significant elevation gain; finisher medals, podium awards, and post-race food are provided.

Enjoy scenic trails around Watchaug Pond at the Li'l Rhody Runaround on November 15, 2026, with 8 mile and 4 mile course options. Part of the WTAC Fall Trail Race Series, it welcomes runners of all levels.

A 13.1 miles trail race in Roosevelt Forest, Stratford, run as eight 1.64 miles loops on marked singletrack and doubletrack. The event features a children's book drive, costume prizes, participant medallions and podium awards for top finish..

Join the Soul n Body Thanksgiving Trail Run in Wolcott CT for a spirited 3.5 mile loop around Mill Pond Way, complete with finisher medals, swag and post race yoga. Proceeds benefit endometriosis research and furry friends are welcome.

TARC Winter Classic offers 8 32 and 40 mile trail races on the rugged Middlesex Fells Skyline Trail with roots, rocky climbs and occasional Boston skyline views. Affordable entry and proceeds support land conservation.

A timed out and back event on the Tower Trail at Sleeping Giant State Park where runners repeat roughly 3.3 mile laps to the Observation Tower in four hour or eight hour formats. Aid is at the start and finish and the race follows a cupless..

A 5K trail event at Roosevelt Forest in Stratford on December 19, 2026. Holiday costumes are allowed, awards go to the top three men and women, and all finishers receive a commemorative medallion. The field is limited and registration is fi..