Trail Running calendar near Fitzwilliam 2025-2026

Join a scenic road and rail trail run with prizes for top finishers. Route may change for weather and the event will be canceled if it snows. Entry is donation based; proceeds benefit a local dog rescue and community theater.

The Toonerville Trail Turkey Trot 5k will take place in Springfield on Thursday 27 November 2025. You can run 5 kilometers.

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..

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..

Krampuslauf - Lyme, NH (December 6, 2025) Krampuslauf is a running event held at the Dartmouth Skiway in Lyme, New Hampshire, with the start area at the ski lodge near 39 Grafton Turnpike Rd. The event offers these distances: 10K 9-hour ev..

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..

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..

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.

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.

Run the Tortoise and the Hare Trail Races on April 4, 2026 at Lions Park in Salisbury with 10K, 5K and a fun 1 mile color run. Family friendly trails, music and post race treats with proceeds supporting Salisbury Parks and Recreation.

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..

The Merrimack River Trail Race is a USATF-sanctioned 10-mile out-and-back trail run held in Andover, Massachusetts, starting from the DoubleTree by Hilton Hotel parking lot. The course features water stations at miles 2, 4, and 8, with a mi..

Event overview The Runamuck 50K is held in South Pomfret, Vermont, with starts and finishes at Saskadena Six. The course covers 3,726 vertical feet and passes through Pomfret and Barnard. Weather on race day can include wind, rain, mud and..

Event overview Spring Fever takes place Saturday, April 11, 2026, at Wompatuck State Park campgrounds in Hingham, MA (204 Union St). Registration closes Friday, April 10 at 11:59 PM ET. The event offers the following distances: 5K 5M 8-Hou..

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.

Event overview The TARC Spring Classic is a trail race held at Jericho Town Forest in Weston, Massachusetts (start/finish: 292 Concord Road). Distances offered are 10K, Half Marathon, Marathon, and 50K, plus a free youth fun run and discoun..

The Dandelion Dash will take place in Hadley on Sunday 3 May 2026. You can run 5 kilometers.

TARC Wapack and Back in Ashburnham MA on May 9 2026 features 21.5, 43 and 50 mile runs along the rugged Wapack Trail with big elevation and wide views to Boston and surrounding ranges. Expect technical terrain and backcountry challenge.

The Wildcat 5K Trail Run-Walk-Wag is an annual event held in Boxford, Massachusetts, starting and finishing at the Danvers YMCA Camp overlooking scenic Stiles Pond. The race features separate courses for runners and walkers, including those..