Trail Running calendar near Roxbury 2026-2027

A 123-mile point-to-point ultramarathon across Connecticut with a 36-hour limit, a mix of trails and roads, multiple mid-course cutoffs, and solo and relay options; finishers receive a buckle, medal, and event t-shirt.

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.

A weekly Northampton cross country series held April through August on an accurately measured 5 km course through fields and woods. Day of registration is required, with modest fees and a season pass option.

A USATF sanctioned 10-mile out-and-back trail race in Andover, MA on April 11, 2026, featuring on-course water stations, homemade prizes and age-group awards, post-race refreshments and a raffle, with proceeds supporting Merrimack River Tra..

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.

A 50K ultramarathon at Saskadena Six in South Pomfret, VT, featuring about 27 miles of dirt roads, 3,726 feet of climb, variable footing and weather, two main aid stations, a water stop, and an 8-hour cutoff.

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.

A spring trail race at Grafton Lakes State Park in Grafton, NY, covering 15K (about 9.3 miles) with roughly 900 ft of elevation gain. Trails are technical but runnable and can be muddy in spring.

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 student run community event on April 25, 2026 at MacDuffie School in Granby, MA featuring a flat cross country 5K and an optional Color Run, with 100% of proceeds going to Dakin Humane Society.

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.

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 the original Spartan Trail Race through the steep climbs and winding trails of the Green Mountain National Forest. Choose from distances between 10 and 200 miles for a true endurance test in Pittsfield Vermont.

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.

A trail race on Winant Park Trails near downtown Concord with windy singletrack, switchbacks, and nordic type paths. Two distances are offered and proceeds benefit the Ralph Waldo Emerson School for Preschoolers; day of event entry is avail..

Trail races in Rollinsford, NH along the Salmon Falls River, offering a canicross 5K, a 5K, and a 5 Miler. Courses mix rail trail, single track, and open fields, with an aid station and specific rules for dog teams.