Trail Running calendar near Boxford 2025-2026

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.

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.

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..

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.

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.

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..

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 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.

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..

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

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..

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 a scenic 3 mile trail through farmland and finish among the vineyard vines at Westport Rivers Winery, then enjoy wine, BBQ, live music and a souvenir glass. Race entry is 21 and over while BBQ options welcome families.

Explore scenic trails south of Sebago Lake at the inaugural Otter Pond Trail Races in Standish, Maine on June 13, 2026. Choose a timed endurance Dawn to Dusk challenge, a 10K or a kids run while supporting Bonny Eagle Athletics.