Trail Running calendar near Stoneham 2025-2026

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 on December 20 invites runners to tackle between one 5K loop and the full ten loop 50K in a festive, low key winter setting. Enjoy scenic roads and trails, event swag and a seven hour limit.

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.

Join Ramsey's Run, a scenic 5k trail run through the woods in Kingston MA on Saturday March 14, 2026. This memorial event honors a Class of 2023 student and raises funds for a scholarship established by the family.

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.

Test your trail skills on the Northern Nipmuck Trail Race, a rugged 16 mile out and back through Yale Myers Forest and Boston Hollow with technical terrain and serious climbing. Limited to 100 entrants, proceeds support local trails.

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.

Hit the trails at Wompatuck State Park in Hingham MA with 5K, 5 mile and 8 hour lap options for all abilities. Expect muddy April trails, on course aid and a community feed, with registration closing April 10 and a 50 runner cap for the 8 h..

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.

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.

Explore trails around Soapstone Mountain and Shenipsit Forest at the Soapstone Mountain Trail Races in Stafford Springs, CT on May 17, 2026. Pick a half marathon or 6K, support local trail stewardship, and register January 1, 2026.

Take on the Drummer Hill Trail Races in Keene NH on May 23, with a 12.5k loop you can repeat for 12.5K, 25K, 37.5K or 50K. Expect technical single track, rocks, roots and stream crossings, aid stops and DHTR drumstick awards.

Experience the 9th annual Wildcat 5K Trail Run, Walk and Wag on May 30, 2026 in Boxford, a scenic 5K around Stiles Pond through Wildcat State Forest. Runners, walkers and their dogs will enjoy trails, prizes and a festive post race celebrat..