Trail Running calendar near Boston 2026-2027

A winter trail event at Hale Education in Westwood offering a 30 hour ultrarun and a 15 mile looped course. The course uses three marked five mile loops, cupless aid stations, strict cold weather gear rules, and limited entry.

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.

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 low key out and back trail race in Union, Connecticut, following the Nipmuck Trail for about 16 miles of technical, hilly terrain with minimal aid stations and a cap of 100 runners. Proceeds support local trail stewardship.

CT123 is a point to point 123 mile ultramarathon across Connecticut, blending trails and backroads for a scenic, challenging adventure. Choose solo 200K or 100K or team relay options, and earn a buckle or medal plus a 2025 race tee.

Trail races in Salisbury on April 4, 2026, featuring 10K, 5K and a one-mile non-timed color run; net proceeds support Salisbury Parks and Recreation. Shirts, awards, post-race snacks and music are included.

Join the Merrimack River 10 miles on April 11 for a USATF sanctioned out and back trail race starting behind the DoubleTree in Andover. Enjoy water stops, post race bagels and a raffle while supporting local trail maintenance.

Trail running at Wompatuck State Park offering 5K, 5M, and an 8 hour lap option limited to 50 runners. Staggered starts, aid stations, drop bags, no dogs, and registration closes April 10.

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 three-race 5K series at White Barn Farm in Wrentham, MA, held across spring, summer and fall. Each trail event reflects seasonal conditions and a Grand Prix combines results for awards and a gift bag at the final race.

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.

The Rescue Run: Race for Marine Mammals will take place in Rye on Saturday 2 May 2026. You can run 5 kilometers.

The Big A 50K is a three-loop trail race on Mount Agamenticus with technical single track terrain and 5,787 feet of elevation gain. Shorter finish points are available and runners are expected to plan to finish within 10 hours.

A trail event at The Hartsbrook School in Hadley featuring a 5K Dandelion Dash and a 1 mile Mushroom Mile. Proceeds support school land stewardship and a virtual 5K option is offered.

Hit the trails at the Cape Cod Trail Race on May 3, 2026, with 10K, 20K and 30K options through the scenic Frances A. Crane Wildlife Management Area. Register soon for a community focused day of challenging trails and postrace camaraderie.

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..

Watuppa Trail Races on May 9, 2026 in Fall River MA offers scenic, runnable trail courses through the Watuppa Reservation with fast grassy fire lanes and winding single track. Distances include 10K, 30K, and 50K.

A trail running event in Rollinsford, New Hampshire featuring a *5 Miler*, a *5K*, and a Canicross 5K with rail trail and single-track sections along the Salmon Falls River.

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