Trail Running calendar near Winchester 2026-2027

A Trail Animals trail event at Hale Education in Westwood offering a timed six hour option and a 3.5 mile singleloop on mostly singletrack around ponds. One cupless aid station at start/finish and limited parking with possible walking.

A classic 16-mile trail run on Connecticut's Nipmuck Trail, known for its technical terrain and old-school vibe. Organized by the Shenipsit Striders, the event supports local trail stewardship. Registration is capped and no race day signups..

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

Experience a festive trail race in Salisbury this Easter weekend. Choose between timed 5K and 10K trail runs or a vibrant 1 mile color run that supports local parks and recreation.

Ascend twenty two floors at the Omni Providence Hotel during 이 premier indoor stair climbing event. Participants can join the open or firefighter categories to tackle three hundred and forty eight steps at their own pace.

Experience a USATF sanctioned 10 mile out and back trail run along the Merrimack River. Enjoy a community atmosphere with unique homemade prizes and support local trail maintenance efforts in Andover.

Experience an obstacle course race in Cumberland featuring a 3.2 mile loop with 1000 feet of elevation. Choose from competitive waves, multilap options, or a signature 12 hour ultra endurance challenge.

Shake off winter at the Spring Fever trail run in Wompatuck State Park. Choose from a 5K, 5M, or 8-hour ultra on a reversed course. All finishers get a custom award and can enjoy on-course support.

Test your endurance on a scenic five kilometer trail loop in Wrentham Massachusetts. This supported race offers forty and fifty mile challenges with a twelve hour cutoff and consistent access to aid stations.

The 11th Annual F.O.R 5k Trail Race takes runners through the scenic McDonald Nature Preserve in Wilbraham. This family-friendly trail run supports the local parks' maintenance fund.

A trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

A 12 mile out and back trail race on the Holyoke Ridge near Amherst MA featuring technical singletrack, over 3,500 feet of ascent, a 500 runner cap and a waitlist when full.

Support marine mammal rescue by running through the scenic forests and rocky shores of Odiorne Point State Park. This family friendly event features a chip timed 5K trail race, kids fun runs, and a community beach cleanup.

The Big A 50K Trail Race is a challenging loop course on Mount Agamenticus with technical, rocky terrain and significant elevation. Participants can choose their distance, from 10 miles up to the full 50K. The event is free to register for,..

Celebrate National Truffle Day with a chocolate themed trail run at Giddings Park. This event features a three loop 5K for all ages and a kids fun run to support Franklin Elementary School programs.

Experience a trail run or walk through the campus of The Hartsbrook School in Hadley. Choose between a 5k or a 1 mile race on natural terrain while supporting local land stewardship and agricultural education programs.

Experience an all trail race through the scenic Frances A. Crane Wildlife Management Area. Choose between 10K, 20K, or 30K distances on a repeating loop course in East Falmouth.

A technical trail race on the Wapack Trail in Ashburnham, MA on May 9, 2026, offering 21.5, 43 and 50 mile options over rocky single track and significant elevation. Registration is limited, manually timed, and nonrefundable.