Trail Running calendar near Nottingham 2026-2027

Experience the peak of New England autumn on a journey through the mountains and fields of central Massachusetts. This trail event offers three distances crossing state borders for runners seeking adventure on the Midstate Trail.

On October 11, 2026 the HFC Striders Cross Country Festival returns to Wayland for its 20th running, featuring 3K youth races across age groups and two 5K open races, with awards and proceeds benefiting Wayland High School.

A rugged trail race at Pawtuckaway State Park featuring technical terrain, boulders, streams and a rocky climb. It offers a half marathon and a 5 mile option and lists $7500 in prize money for 2026.

Experience New Hampshire’s original 30 hour ultramarathon on the historic Granite Town Rail Trail. Choose from multiple distances and relay options in this flat and fast Halloween themed fundraiser for local trail conservation.

A mountain running event in North Conway, NH on October 17, 2026, featuring two race options on Cranmore Mountain and $7500 in cash prizes. The course uses ski slopes, singletrack, and service roads and includes one aid station.

A six hour weighted lap race on Mansfield's WWII Veterans Memorial Trail. Competitors carry measured weight each lap and score pound-miles called Kz, with the highest total in each division winning.

A trail race at East Windham Conservation Area offering a five-loop 50k and a one-loop 10k; each loop is about 10k with roughly 900 ft of elevation gain and two aid stations.

Join a community trail race through the diverse terrain of Wompatuck State Park. Choose between a ten mile loop or a 50K distance on a course featuring rail trails and single track paths.

A harvest-season 5K trail event at White Barn Farm in Wrentham with off-road terrain, a midway water station, bib pick-up the day before, family Harvestween activities, and a portion of registrations donated to the local food pantry.

A 5K on October 24, 2026 at Stratham Hill Park that runs along Great Bay and benefits Great Bay Stewards; the mostly downhill course includes a race shirt for timely registrants and a bib with a beer or cider coupon.

A mountain trail race in Keene NH on October 25, 2026 covering 4.9 miles with 1,650 feet of elevation across four laps; the event benefits the Keene Community Kitchen and offers prize money, age-group awards, and raffles.

A fall trail race at Powisset Farm in Dover on October 25 2026 offering four distances, one water aid station, post race cider donuts and family activities with awards for top finishers.

A fall trail event in Harvard on October 25, 2026 featuring a 5K through orchard and woods plus a 1 mile kids fun run, with age divisions, awards, shirts, and proceeds benefiting the Harvard Conservation Trust.

A stair climb at Gillette Stadium where participants walk, jog or climb around the lower bowl while music and team highlights play. Net proceeds support Homes for Our Troops.

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 backyard ultra at Kenty's Farm on November 7, 2026 where runners complete repeated 4.1666 mile laps until one remains; also offers 6, 12 and 24 hour timed options and a single-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.