Trail Running calendar near Springfield 2025-2026

Run for the Hills in Harvard, Massachusetts is a pair of off‑road trail races held at the Community Harvest Project Orchard (115 Prospect Hill Rd). The event features a challenging 5K trail run through orchard, woods, and fields, plus a 1‑m..

Join The Hamsterwheel in New Boston NH for a friendly 4 mile loop ultrarun with 6, 12, 24 and 30 hour solo and relay options. Scenic rail trail, night running, team camaraderie and quirky buckles make it a fun intro or a bold challenge.

Join the 9th annual Fall Back into the Trails at Red Wing Recreation Area in Lagrangeville NY for two days of scenic, supported loop trail racing with 10K 50K and 100K options. Custom finisher medals, camping and UTMB index for longer races..

Run through the vines at Stonington Vineyards in this chip timed 5k that finishes with a wine pour, unique finisher medal, and a shatterproof wine glass. Two laps through scenic vineyard trails make it perfect for runners and walkers.

Overview 8 Hours at the Farm is a timed trail running event presented by Steep Endurance on November 2 in Brookfield, Connecticut. The event is held at Gurski Farm / Williams Park with race headquarters and the start/finish located in the b..

Race for DFL is a last-runner-standing backyard ultra held at Kenty’s Farm in Winchendon, Massachusetts. The event uses a single lap of about 4.17 miles, with a course mixture of grassy field, forest trail, crushed gravel bike path, and a d..

Raven Rocks Run (10k) at Ward Pound Ridge Reservation The Raven Rocks Run is a trail event held at Ward Pound Ridge Reservation in Cross River, NY. The in-person event includes a 10k trail run that climbs to the park's high points, passing..

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,..

Take on scenic but technical, hilly single track trails in Upton State Forest with 10.5K or 21K (two laps) options on Sunday November 9, 2025. Field is limited to 250 runners and online pre registration closes November 7.

Join the TARCkey Trot, a six hour timed challenge at Wright Locke Farm on November 15, 2025, running multiple 5K trail loops over rocky rollers. Tackle as many laps as you like while supporting land conservation.

Li'l Rhody Runaround Trail Run is held at Burlingame State Park in Charlestown, Rhode Island. It is the fourth and final race in WTAC’s Fall Trail Race Series, offering two trail distances: 8 miles and 4 miles on Watchaug Pond area trails...

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 challen..

Event details The Tarrywile Half Marathon is a trail running event held on November 16 at Tarrywile Park, 70 Southern Blvd., Danbury, Connecticut. The event offers three distances: Marathon Half Marathon 10K Registration tiers vary by dat..

Event details Fall Fling 400 is organized by the CT Trailmixers at YMCA Camp Sloper in Southington, Connecticut on November 22, 2025. The event offers two main entry options: 400-minute run on a roughly two-mile loop 4 Mile (two laps of th..

Run the Novemberfest Race, a scenic 4 mile through Mine Falls Park in Nashua, finishing near the Millyard smokestack. Celebrate at Martha's Exchange after the race while supporting the Nashua Children’s Home.

Brooksvale Trails Turkey Trot : November 23, 2025 The Brooksvale Trails Turkey Trot takes place in Hamden, CT, at Brooksvale Park (524 Brooksvale Avenue). The event is organized by Live Loud Running and the Town of Hamden and is the third a..

Join the Roxbury Thanksgiving Day Charity Race for a festive 5K through Everett B. Hurlburt Community Park. Support local causes and burn off holiday calories with friends and neighbors this Thanksgiving morning.

Turkeywacker 5K is a Thanksgiving morning trail run held in Wrentham, Massachusetts, at the William Rice Recreation Complex (54 Emerald Street). Now in its ninth year, the scenic 5K course winds through the complex’s trail system, welcoming..

Join the Tower Tag Challenge at Sleeping Giant State Park on December 6 for timed 4 or 8 hour trail running on scenic Tower Trail loops. Earn a Ragged Cuts finisher medal, enjoy great views, and support the park.

Event overview The Frosty Forest 5K takes place in Roosevelt Forest in the Town of Stratford, Connecticut on Saturday, December 13, 2025. The event is a trail run over a 5K distance. Participants may wear holiday costumes during the event...