Trail Running calendar near Weston 2025-2026

Join the Mount Hood Nutcracker Challenge in Melrose for a festive 3.5 mile cross country race or 2 mile walk on the Mount Hood golf course. Enjoy nutcracker trophies, pasta lunch and fundraising for local families and Melrose High XC.

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.

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.

Join Ramsey's Run in Kingston MA on March 14, 2026 for a scenic 5k trail run through the woods, timed by a professional company. Honor a class of 2023 member and support a family scholarship with every entry.

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..

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.

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..

Take on the Dandelion Dash 5K or the Mushroom Mile on The Hartsbrook School trails, with a virtual option available. Muddy, scenic terrain and proceeds support the school's Land Stewardship program.

The Cape Cod Trail Race will take place in Falmouth on Sunday 3 May 2026. You can run between 10 and 30 kilometers.

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.