Trail Running calendar near Winchendon 2025-2026

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.

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.

The Dar Snowshoe Scramble will take place in Goshen on Sunday 25 January 2026. You can run 10 kilometers.

Tackle the TARCtic Frozen Yeti at Hale Education in Westwood MA on Feb 7 and 8 2026 with a 30 hour challenge or a 15 mile looped race. Expect well marked winter trails, regular aid and proceeds supporting land conservation.

Run the scenic single track loop at Hale Reservation in Westwood, MA with 3.5 mile or 6 hour options. Trails, pond views and wood bridges await while proceeds support land conservation.

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 will take place in Andover on Saturday 11 April 2026. You can run 10 miles.

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.

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..

TARC Spring Classic in Weston MA on April 25, 2026 offers 10K, half, marathon and 50K trail races plus a free youth fun run on a smooth scenic 10K loop. This cupless, multi lap event fills fast so register early as parking and aid are limit..

Tackle the scenic Seven Sisters Trail Race in Amherst, MA on May 2, 2026, an out and back along the Holyoke Range ridgecrest. This rugged 12 mile course delivers steep climbs, rocky singletrack and over 3,500 ft of elevation for a thrilling..

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.

Run the rugged Wapack Trail in Ashburnham MA with 21.5, 43, or 50 mile options on May 9, 2026. Limited entries for this technical, scenic trail run benefit land conservation through the Trail Animals Running Club.