Trail Running Calendar Connecticut 2025-2026

The Tarrywile Half Marathon, held in Danbury, Connecticut's Tarrywile Park, is known as one of the toughest trail half marathons in the region. Covering nearly 3,000 feet of elevation gain, the course features technical Northeast single-track trails with rocky, rooty, and hilly terrain. Runners enjo..

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 event where participants run as many loops as possible on a roughly two-mile trail course, and a 4-mile race consisting of..

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 the iconic Sleeping Giant State Park in Hamden, Connecticut. The race features a simple yet demanding course on the Tower Trail, a mostly smooth carriage road that ascends over 600 feet in 1.5 miles to the park's Observation Tower, offering st..

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 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 a challenging ultramarathon spanning 123 miles across Connecticut, starting in East Thompson and finishing at the Wakeman Boys & Girls Club in Southport. The point-to-point course traverses 25 towns, combining approximately 57 miles of well-maintained trails with scenic backroads an..

The Jack Bristol Lake Waramaug Ultra Races, held in Kent, Connecticut, is a historic ultra running event celebrating its 52nd anniversary in 2026. It features three race distances: 100K, 50 miles, and 50K, all conducted on primarily flat, rolling loops around scenic Lake Waramaug on paved roads. The..

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..