Trail Running calendar near Windham 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.

Mount Ascutney Vertical Backyard : Nov 22, 2025, Brownsville, VT The event is a "Last Person Standing" format held at Mount Ascutney in Brownsville, VT (449 Ski Tow Rd). Participants complete repeated laps; each hour they must asc..

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.

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..

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..

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..

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.

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 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..

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..

Choose 24 hour, 12 hour or 6 hour timed loops at White Lake State Park in Tamworth, NH on May 2, 2026. Enjoy scenic 2 mile loops with some technical trail and beach sections; this is a cupless event so bring your own hydration.

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