Trail Running calendar near Winchendon 2025-2026

Challenge yourself on a hilly 5K at Melrose High School's home cross country course in Melrose, MA while supporting the school's XC teams. Expect rugged terrain, post race snacks, and lively local race day energy.

Join the Novemberfest Race in Nashua for a scenic 4 mile loop through Mine Falls Park, followed by a lively post race party and raffle at Martha's Exchange. Community focused and fun, the event benefits the Nashua Children's Home.

Tackle a rolling 8K through the West Hartford Reservoir at the Hartford Track Club 8K Cross Country Challenge on Nov 23, 2025. Enjoy trails, gravel and scenic views as runners vie for age group honors in a fast, fun fall race.

Make Thanksgiving morning active at the Turkeywacker 5K in Wrentham, a festive trail run at Rice Recreation Complex with donuts, cider and raffle prizes. Awards for top finishers across ages ensure competition and family fun.

Celebrate Thanksgiving in Springfield VT at Toonerville Trail Turkey Trot, a flat, scenic 5K along the Black River with a virtual option to support local food banks and school teams. Finishers get socks and cider donuts.

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.

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.

Run or walk the Sunday after Thanksgiving at Chesterfield Gorge with a scenic trail 5k, family walk and kids race along the Westfield River. Finishers earn a baked cookie medal and can enjoy a potluck, with proceeds to Hilltown Land Trust.

Join Krampuslauf in Lyme NH for a festive mountain trail run from the Dartmouth Ski Way lodge, offering 5K, 10K and a 9 hour multi lap challenge. Finish loops to earn a 10K medal with pins and upgrades to a 50K medal.

Take on the TARC Winter Classic at Middlesex Fells with 8, 32 and 40 mile Skyline Trail loops featuring roots, climbs and occasional Boston skyline views. Limited spots, cupless aid and winter trail conditions make this a true test for expe..

Take on the scenic Mount Hood golf course in Melrose with a 3.5 mile cross country race or 2 mile walk, limited to 250 entrants. Enjoy varied terrain, nutcracker awards and post race pasta while supporting local schools and Housing Families..

Seth's Fat Ass 50K at Forest Park in Springfield is a friendly challenge of up to ten 5K loops. You have seven hours to run as many laps as you like, grab event schwag and a t shirt, and enjoy the social ultrarunning vibe.

TARCtic Frozen Yeti brings winter trail racing to Hale Education in Westwood, MA on Feb 7 and 8, 2026. Choose a rugged 30 hour endurance challenge or a scenic 15 mile loop and tackle snowy trails under starlight.

Experience scenic wooded loops and pondside views at TARC To Hale and Back in Westwood MA, choose a 6 Hour challenge or a 3.5 Mile loop. The trail mixes singletrack and fire road, features one aid station and is cupless so bring your own bo..

Run a scenic 16 miles on the Nipmuck Trail in Union Connecticut, out and back to the Boston Hollow turnaround through Yale Myers Forest. Field is capped at 100 and proceeds benefit local trail groups.

Run Across CT 123 is a point to point ultramarathon across about 123 miles of Connecticut, weaving trails and backroads through 25 towns. Choose 100K or 200K solo or relay and chase a coveted belt buckle for 200K finishers.

Join the Tortoise and the Hare Trail Races in Salisbury on April 4, 2026 for trail 10K, 5K and a fun 1 Mile Color Run. Enjoy custom tech shirts, post race music and snacks while supporting Salisbury Parks and Recreation.

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..

Runamuck 50K is a rugged trail ultramarathon around South Pomfret, Vermont, weaving hilly dirt roads and scenic backcountry. Expect changeable weather and a true test of endurance on this challenging 50K course.

Spring Fever brings scenic early spring trail racing to Wompatuck State Park in Hingham on April 11, with 5K, 5 mile, and an 8 hour multi lap challenge. Expect muddy trails, on course aid, and a friendly campground finish line vibe.