Trail Running calendar near York 2026-2027

Discover the beauty of Emmons Preserve at a community event featuring trail races and family activities. Enjoy music and local treats while supporting holistic education through a variety of distances for runners and walkers.

A Stadion 5K obstacle race at Fenway Park on November 7-8, 2026, featuring 20 obstacles and a finish across home plate. The weekend also includes a 1 to 1.5 km kids race, spectator tickets, team options, and a service member discount.

A multi hour loop event on the New Boston Rail Trail near the fairgrounds offering 6, 12, 24 and 30 hour individual and relay options, chip timing, a central aid station, team entries, pacer rules and 100-mile buckles.

A November trail festival at Willowdale State Forest in Ipswich offering multiple looped distances from a 10K to 100K, a Cider Donut Mile, and a flagged 0.5‑mile youth run, with cupless aid stations and fundraising for local land trusts.

A last runner standing backyard ultra on private farmland in Winchendon with a 4.1666 mile loop. The event also offers 6 hour, 12 hour and 24 hour timed options plus a standalone fastest lap competition.

A mountain race at Cranmore Resort on November 7, 2026, offering 5 km and 10 km courses on access roads and ski trails, marked with reflective flagging and LED lanterns; headlamps are required and registration is online.

A 6 hour timed trail race on a 5K loop at Wright Locke Farm in Winchester Massachusetts, featuring rocky rolling singletrack, a barn aid station in a cupless format, and provisions for adaptive athletes and youth discounts.

Enjoy a festive four mile trail race through the wide paths of Mine Falls Park. All proceeds from the run and raffle support residential and educational programs at the Nashua Childrens Home.

A Thanksgiving morning trail event in Jackson, New Hampshire featuring a 5k through nordic trails and a 1k kids run for ages 10 and under. Day of registration is available and proceeds benefit local youth programs.

A trail running event at Middlesex Fells Reservation with **8 mile**, **32 mile**, and **40 mile** loop options on the white blazed Skyline Trail. The course is technical and minimally marked, cupless with two aid stations and specific cour..

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.

Experience a winter trail challenge at Hale Education featuring 15 mile and 30 hour options. Navigate three unique loops through the Massachusetts woods while testing your endurance and self reliance in cold weather conditions.

US Snowshoe Nationals 2027 in Concord, New Hampshire features four races over two distances, separate awards including top 3 AGs, a flat course through fields and singletrack, and weekend social events.

The TARC Spring Classic takes place April 24, 2027 in Jericho Town Forest, Weston, MA, with 10K, half marathon, marathon and 50K looped trail options, a single aid station, marked course, and a cupless race format.

A trail running event on the Wapack Trail in Ashburnham Massachusetts with 21.5 mile, 43 mile, and 50 mile options across rocky, technical terrain with aid stations, drop bag support, and a manual timing system.