Trail Running calendar near Stonington 2025-2026

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..

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.

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.

SRC Presents: A Backyard Ultra takes place at Blydenburgh County Park in Hauppauge, NY on December 13–14, 2025. The event features two races: A Backyard Ultra, a true ultramarathon where runners must complete a 4.167-mile loop within an hou..

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..

Brave winter trails at Hale Education in Westwood, MA for the TARCtic Frozen Yeti on Feb 7 to 8, 2026, a scenic tri loop course that returns to the lodge. Choose a 30 hour ultra or a single 15 mile lap and test your winter trail skills.

The Ramsey's Run will take place in Kingston on Saturday 14 March 2026. You can run 5 kilometers.

Event overview The Ospreys Dominion Wine Run 5k is scheduled for Saturday, March 21, 2026 in Peconic, NY at Osprey's Dominion Vineyards (44075 Main Rd, Peconic, NY 11958). The event is a 5k run/walk open to ages 1 through 99. The event is c..

Event overview The Enchanted Forest Ultra Run is a trail ultramarathon held at Roosevelt Forest, 700 Peters Lane, Stratford, CT. The event is offered as a 6-hour format and as a 50K distance. Field size is limited to 50 participants. Regist..

TARC To Hale and Back features a scenic 3.5 mile loop through woods and shoreline with roots, rocks and a few modest hills. Pick a timed 6 hour challenge or the single loop and enjoy a friendly aid station and strong volunteer support.

Run 16 miles of rugged single track through Bigelow Hollow and Yale Myers Forest to Boston Hollow in this intimate, capped trail race near Union, CT. Limited to 100 runners, the event supports local trail organizations.

Event details The Sleeping Giant Trail Runs take place March 29, 2026 at Sleeping Giant State Park, 200 Mt Carmel Ave, Hamden, CT. The event offers these distances: 25K 50K (two loops of the 25K loop) Registration closes March 27. Entry f..

Run Across CT 123 is a scenic 123 mile ultramarathon across Connecticut from East Thompson to Southport, weaving through forest trails and backroads. Enter as a timed solo or relay team and challenge yourself to finish within the 36 hour cu..

Run scenic singletrack at Penwood State Park in the Traprock 17 km and 50 km Ultramarathon, a friendly community race with short and long course options. Race day is the Saturday before the Boston Marathon.