Trail Running calendar near Pomfret 2025-2026

Run or stroll through historic Alice Newton Street Park at the Woodbridge Trail Run plus Woodland Walk, with a challenging two loop 4 mile course and an easy 2 mile walk to the falls. Participants receive custom tech T shirts and post event..

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..

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.

Windham Woods School Thankful Trails 5K Run & Walk Windham Woods School hosts the 2nd annual Thankful Trails event on November 15, 2025, at 39 Roulston Road, Windham, NH. The event includes a 5K trail run/walk and a Kids Fun Run for chi..

Run scenic trails around Watchaug Pond at Burlingame State Park with 8 mile and 4 mile options in the Lil Rhody Runaround. Close out the WTAC Fall Race Series while soaking up classic New England fall scenery.

Take on the Baystate Dirty Dog Trail Run Ruck Walk 5k in Berkley on November 16, a rugged, possibly muddy trail where you can run, ruck with a pack, walk, or bring a leashed dog. Proceeds support local beagle and K9 charities.

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..

Celebrate Thanksgiving on the trails at the F.I.T. Turkey Trot Trail Race in Cumberland, Rhode Island on November 27. Choose from 5K, 5 Mile, combo, multilap or a Kids Race and earn a unique finisher medal.

Event details The TARC Winter Classic takes place Saturday, December 6, 2025, at Middlesex Fells Reservation in Stoneham, Massachusetts. Distances offered are: 8 mile 32 mile 40 mile Online registration closes at the beginning of race wee..

Test your endurance at the Tower Tag Challenge in Sleeping Giant State Park with 4 hour and 8 hour timed options on repeated 3.3 mile loops to the Observation Tower. Bring your own cup, enjoy finisher swag, and support the park.

The Mount Hood Nutcracker Challenge is an annual cross-country running event held at the Mount Hood Golf Club in Melrose, Massachusetts. This unique 3.5-mile race features a challenging, hilly course that changes every year, incorporating f..

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...

Run Seth's Fat Ass 50K on Saturday December 20 2025 at Forest Park in Springfield MA, a friendly looped ultra offering one to ten 5K laps with a seven hour cutoff. Relaxed vibe, easy parking and race day registration welcome runners of all..

Event overview The West Rock Winter Fat Ass Extravaganza is scheduled for December 28, 2025 in Hamden, CT near Lake Wintergreen. The event is an eight-hour looped run using a 1.6-mile loop around Lake Wintergreen with about 65 feet of eleva..