Trail Running calendar near Springfield 2025-2026

The Stonington Vineyards Wine Run Turkey Trot 5k is a festive running event held at Stonington Vineyards in Stonington, Connecticut. This chip-timed 5k features a two-lap cross-country style course that winds through vineyard lanes, offering scenic views and some uneven terrain suitable for both run..

The Race for DFL is a unique "last runner standing" backyard ultra event held at Kenty’s Farm in Winchendon, Massachusetts. Participants run a 4.1666-mile loop every hour on the hour, continuing until only one runner remains. The course features a mix of terrain including grassy fields, trails, crus..

The Upton Half Marathon Trail Race, held in Upton State Forest, Massachusetts, offers a challenging and scenic trail running experience. Participants can choose between a 10.5K or a half marathon distance, with the half marathon consisting of two laps of a 6.5-mile course featuring technical, hilly..

The Raven Rocks 10k Trail Run is an annual challenging trail race held at Ward Pound Ridge Reservation in Cross River, NY. The course features rugged terrain with rocky climbs, ridgeline trails, hilly meadows, and ravines, ascending to the park's two highest points: Raven Rocks Overlook and the Fire..

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 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 will take place in Charlestown on Sunday 16 November 2025. You can run between 4 and 8 miles.

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 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 will take place in Southington on Saturday 22 November 2025. You can run between 4 and 6 kilometers.

The Novemberfest Race is an annual 4-mile running event held in Nashua, New Hampshire, featuring a scenic course through Mine Falls Park. This community-focused race supports the Nashua Children's Home, with all proceeds benefiting the organization. The event also includes a raffle held at Martha's..

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 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..

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 John Jay Community Trail Race, held in Cross River, NY, is a competitive 5k run on the newly developed John Jay Community Cross Country Trail. The course begins on the lower fields of the John Jay Campus, quickly entering challenging, hilly wooded trails near the middle and high schools, and fin..

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..

Leatherman's Loop is a popular 10K trail race held annually in the spring at Ward Pound Ridge Reservation in Cross River, New York. The event attracts runners aged 7 to 107 and features a scenic course through natural trails. Due to high demand, entry is determined by a lottery system.The registrati..