Trail Running calendar near Holyoke 2025-2026

The TARCkey Trot is a unique 6-hour timed running event set on a scenic 5K loop at Wright Locke Farm in Winchester, MA. Participants can run as many loops as they wish within the time limit, navigating a course filled with natural terrain challenges. The event promotes community engagement, offering..

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 Tarrywile Half Marathon, held at Tarrywile Park in Danbury, Connecticut, is a challenging trail race known for its significant elevation gain of nearly 3,000 feet and technical Northeast single-track terrain. The course offers stunning views of Danbury and the park's tranquil lakes. The event fe..

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 27th Annual Novemberfest Race for the Nashua Children's Home is a festive 4-mile run through Mine Falls Park in Nashua, New Hampshire. The course winds through scenic park terrain, with the start/finish area near the Pine Street Extension Entrance about 200 yards west of the Millyard Smokestack...

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..

Tower Tag Challenge takes place at Sleeping Giant State Park in Hamden, Connecticut. The course centers on the Tower Trail, a crushed-gravel carriage road that climbs about 600 feet in 1.5 miles to the Observation Tower. The race is run purely up and down the Tower Trail, with a short paved section..

The Frosty Forest 5K is a trail running event held in Roosevelt Forest, Stratford, Connecticut. This 5-kilometer 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 exp..

The TARCtic Frozen Yeti is a winter trail running event hosted by the Trail Animals Running Club at Hale Reservation in Westwood, Massachusetts. Scheduled for February 7-8, 2026, it offers two distance options: a 15-mile race and a challenging 30-hour ultra. The course features three roughly 5-mile..

Located in Union, Connecticut, the Northern Nipmuck Trail Race is a 16-mile ultramarathon staged just outside Bigelow Hollow State Park. The course runs south on the Nipmuck Trail through the Yale-Myers Forest, crosses Barlow Mill Rd at mile 4, then reaches a turnaround at Boston Hollow before retra..

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 featuring over 3,000 feet of vertical gain, and a 50K option consisting of two loops...

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..

Jack Bristol Lake Waramaug Ultra Races run around Lake Waramaug in Kent, Connecticut, offering 100K, 50M, and 50K. One of the oldest ultras in the United States, it marks its 52nd anniversary in 2026 as part of the Mount to Coast 100K Series. The rolling, mostly flat course uses paved roads around t..

The TARC Wapack and Back is a challenging trail running event held annually in Ashburnham, Massachusetts, along the scenic Wapack Trail. Offering three distance options—21.5 miles, 43 miles, and 50 miles—the race features rugged terrain with rocky ledges, boulder fields, granite slabs, and technical..

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..