Winchester
Trail Running Calendar near Winchester 2026-2027
Explore the top trail runs near Winchester for 2026-2027! We've gathered 40 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
Obstacle-course weekend at Fenway Park with a Stadion 5 km (20 obstacles), kids races and spectator access on November 7-8, 2026.
A November trail festival at Willowdale State Forest offering races from 10K to 100K, a cider donut mile, and a free youth fun run.
A November trail event in Hingham MA offering a single 4 mile loop, an open 8 hour loop-count race, and a Backyard style hourly format that allows missed cutoffs.
A hilly 5K at Pine Banks Park in Melrose supporting Melrose High School cross country teams, with overall and age group awards and post race refreshments.
Six-hour timed trail race on a 5K loop at Wright Locke Farm in Winchester MA with rocky rollers, a cupless barn aid station, and a youth discount.
Third annual Thankful Trails 5K at Windham Woods School on November 14, 2026, features a two loop trail 5K and a free kids fun run on the lower field.
A community trail event at Good Pickin’ Farm with a scenic 5 mile run, a 2.5 mile walk or run, and a 1K kids run plus post race farm activities.
Trail races of 5.3 miles and 10 miles through Callahan State Park with road sections to and from Brophy Elementary in Framingham.
A community memorial run in Tyngsboro, MA with a 1.5-mile walk and two 5K options, raising funds for a school scholar/athlete award and science scholarships while maintaining a tradition of food donations.
A 4 mile trail race in Mine Falls Park with a post race party, raffle, awards, and proceeds supporting the Nashua Children's Home.
Thanksgiving Day 5K cross-country run/walk at Maudslay State Park supporting local charities, organized by Joppa Flats and Winners Circle Running clubs.
A scenic 5K trail run in Wrentham, MA on November 26, 2026 with awards, post-race donuts and cider, a raffle, and a $25 registration fee.
December 2026
Celebrate the twentieth anniversary of this unique cross country race held at the Mount Hood Golf Club. Choose between a competitive three and a half mile run or a festive two mile walk through hilly terrain.
January 2027
Winter trail event at Hale Education in Westwood with a 30 hour ultra and a 15 mile looped course, marked trails, cupless aid stations, and required cold weather gear.
April 2027
USATF sanctioned 10 mile trail race in Andover MA with timed results, aid stations, baked prizes, and proceeds supporting Merrimack River Trail maintenance.
Trail Animals Running Club hosts looped trail races at Jericho Town Forest with 10K, half marathon, marathon and 50K options, a single aid station, and strict time cutoffs.
June 2027
A 20 mile single loop hike at Wompatuck State Park on June 5, 2027, featuring aid stations, a finisher medal, certificates, and varied trail terrain.
October 2027
Test your endurance on a scenic 5K trail loop in Wrentham where you decide how far to go one hour at a time with distances ranging from 5K to 50K.