Trail Running calendar near Winchendon 2025-2026

Join the Gorge après Gorge for a scenic 5 km trail run or Family Fun Walk at Chesterfield Gorge the Sunday after Thanksgiving. Enjoy handmade hats and cookie medals, a community potluck with hot drinks, and support Hilltown Land Trust.

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..

Join Krampuslauf on December 6, 2025 at Dartmouth Skiway in Lyme NH for trail 5K, 10K or a multi lap endurance challenge. Festive mountain scenery, indoor lodge support and proceeds benefit Vermont Adaptive Ski and Sports.

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.

TARC Spring Classic offers scenic trail loops in Jericho Town Forest, Weston MA with distances from 10K to 50K. Run with the Trail Animals Running Club to support land conservation; spots sell out, so enter early.

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

TARC Wapack and Back is a rugged ridge trail race on the Wapack Trail with 21.5, 43 and 50 mile options over rocky, technical terrain and big climbs. Expect minimal markings and serious elevation so seasoned trail runners only.

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..

The Fitzwilliam to Troy Depot Day Cheshire Rail Trail Fun Run will take place in Fitzwilliam on Saturday 6 June 2026. You can run 5 miles.

Enjoy the Nipmuck South Trail Race in Mansfield CT, a 15.7 mile out and back along the Fenton River that winds through woods, fields and over small bridges. Organized by Shenipsit Striders, proceeds benefit local trail stewardship.