Trail Running calendar near Brattleboro 2025-2026

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.

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.

Join Trail Animals Running Club Winter Classic at Middlesex Fells for scenic but rugged Skyline Trail loops with 8, 32, and 40 mile options. Expect rocky climbs, limited aid, cupless racing, and a friendly sold out vibe.

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.

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.

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.

Run a scenic 6.55 mile quarter marathon through West Hartford Reservoir 4 as two loops around the park. Limited to 150 runners, the event features chip timing, post race treats and awards in five year age groups.

Tackle rugged trails at Penwood State Park in Bloomfield CT with the Traprock race, offering a single loop 17K or a three loop 50K on scenic, rocky Metacomet Trail. Hosted by CT Trailmixers, this cupless trail run supports local land trusts..

Run the TARC Spring Classic at Jericho Town Forest on April 26, 2025, choosing distances from 10K to 50K plus a free youth fun run. Enjoy a smooth, relatively flat looped trail with one aid station offering vegan friendly options.

Run the scenic Dandelion Dash 5K on The Hartsbrook School trails or enjoy the family friendly Mushroom Mile in Hadley, MA. Support school programs in sustainable agriculture and beekeeping or run virtually from anywhere.

TARC Wapack and Back is a scenic, rugged trail race in May on the Wapack Trail between Massachusetts and New Hampshire, offering 21.5, 43 and 50 mile options. Expect technical terrain, big climbs, limited aid, and a tight knit trail communi..

Run the Free Spirit 50K in Leyden, Massachusetts and enjoy a scenic New England ultramarathon. The course follows dirt roads past historic farms, leafy woods and an 1870s covered bridge for a rewarding, challenging day.

The Canterbury Shaker Village XC 5k will take place in Canterbury on Saturday 16 May 2026. You can run 5 kilometers.

Enjoy a scenic 5k at Ledge Rock Hill Winery in Lake George with a cross country style course and options to volunteer and run. Finishers get a medal that doubles as a wine stopper, a shirt and a wine pour.

Run a scenic 5 mile route along the Cheshire Rail Trail from Fitzwilliam Depot to the restored Troy Depot while supporting the Fitzwilliam and Troy Historical Societies. Food, festivities and a short kids loop make it a great community day.

Run or ride scenic farm trails at Norbrook Farm Brewery in Colebrook CT, with options from a 5K and 10K to a 4 hour trail challenge, duathlon and competitive mountain bike races. Finishers get custom medals and entrants 21 plus receive a fr..