Trail Running calendar near Chesterfield 2026-2027

A 4.9 mile mountain trail race in Keene, NH on October 25, featuring four up and down laps on different trails, 1650 feet of elevation, prize money and age group awards, with proceeds supporting the Keene Community Kitchen.

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 trail half marathon at Moreau Lake State Park near Gansevoort NY, covering roughly 14 miles with 2700 feet of gain on technical singletrack. The course is fully marked, includes an aid station about six miles in, and has beach parking.

A 10K trail race at Penwood State Park in Bloomfield, CT on November 1, 2026. The rolling loop follows mostly technical single track on the Metacomet, Orange and Yellow trails, has no on course aid station and a three hour cutoff.

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.

Timed running event offering several durations in New Boston, NH on a 4.0 mile loop along the New Boston Rail Trail. Chip timing, a central aid station, 100 mile buckles for individuals and teams, and specific pacer and camping rules apply.

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.

Two trail races in Upton State Forest offering a 10.5K loop and a half marathon of two 10.5K laps. Technical single track and forest roads with about 720 ft climb per lap and aid stations roughly every 3 miles.

A family friendly run and walk at West Thompson Dam on November 8, 2026 featuring a timed 5K trail run, a 3K untimed walk and a free kids 1/4 mile run; proceeds support local trails, parks and a food pantry.

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.

A Last Person Standing mountain event with hourly 2.25 mile laps that climb about 1,209 feet each. Aid, hot food, camping, elevation milestone prizes, and awards are provided; conditions may include cold, snow, or ice.

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 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..

Krampuslauf brings a Krampus-themed running event to Dartmouth Skiway in Lyme, New Hampshire, with 5K and 10K loops and a 9 hour 10K lap challenge. Finishers receive medals and lap runners collect pins and a 50K medal.

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.

Experience the US Snowshoe Nationals in Concord New Hampshire. This winter event features 5k and 10k races on a flat and fast course through open fields and singletrack trails.

On March 28, 2027 this roughly 16 mile out and back follows the Nipmuck Trail through Yale Myers Forest and Bigelow Hollow State Park. Registration opens Jan 1, 2027, parking is limited and a waitlist is used.

A point-to-point ultramarathon across Connecticut, Run Across CT 123 covers about 123 miles from East Thompson to Southport with trail and road sections, a 36-hour cutoff, solo and relay options, volunteer-supported aid stations, and finish..