Trail Running calendar near Chester 2026-2027

The Runamuck 50k returns to the hills of Vermont. This challenging 50K course starts and finishes at Saskadena Six, featuring 27 miles of rolling dirt roads. Be prepared for variable footing and classic New England spring weather.

A fast, point-to-point half marathon descending from Slingerlands to the Hudson River in Albany. The course features paved rail trails and offers amenities like live tracking, gear check, and a post-race celebration. A free shuttle bus mana..

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.

The Grafton 15K is a spring trail race through the technical and muddy terrain of Grafton Lakes State Park. The 9.3-mile course features 900 feet of elevation gain, starting and finishing at the park's beach.

The Mucker offers a choice of trail adventures in Hubbard Park, from a 5k hike or ruck to a 5k or 5-mile run. It's part of the Montpelier Mudfest weekend. A kids' obstacle course event runs concurrently on the State House lawn.

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.

Take on the trails at the Hartsbrook School for the Dandelion Dash 5K or the family-friendly Mushroom Mile. This community event supports the school's unique Land Stewardship program. A virtual run option is also available.

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..

The Free Spirit 50K is a scenic ultra on the dirt roads of Leyden, Massachusetts. The route passes historic farms, forests, and a vintage covered bridge, offering a classic New England countryside experience.

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

The Steel Rail Races feature a marathon, half marathon, and 8K on the scenic Ashuwillticook Rail Trail in Adams, MA. Runners enjoy a technical shirt, finisher medal, and a post-race party with live music. The event supports the maintenance..

Hit the trails at Pittsfield State Park for the Tails & Trails State Forest Run. Choose from 50K, 25K, or 5-mile distances on a scenic loop course. The event supports local animal rescue organizations.

A point-to-point 50-mile ultramarathon from Manchester to Monadnock State Park, featuring over 6,000 feet of elevation gain. The course mixes roads, dirt roads, and trails, and requires GPX navigation. With limited spots, runners must plan..

Event Overview The Ledge Rock Hill Wine Run 5K takes place at the Ledge Rock Hill Winery in Lake George, New York. The event features a 5K distance, which is open to participants aged 1 to 99. It is a timed race, with professional timing an..

A series of rugged trail races in Ripton, Vermont from May 21 to 31, 2026 offering distances from 9 miles to 250 miles plus multi‑marathon and ultra challenges. Camping is available for a one time fee; the event is cup free and no refunds.

Choose your own adventure at the Drummer Hill Trail Races in Keene, NH. Run a flexible number of 12.5k laps on technical, hilly trails, with distances from 12.5K to 50K. Aid stations and a cupless policy support your run through scenic wood..

Experience the natural beauty of Montpelier North Branch Park at the Birdland 5K. Run through rolling singletrack and forested hills in this cupless trail race designed for environmental conservation.

The Chocorua Mountain Race is a rugged 23K adventure in New Hampshire's White Mountains, featuring 4,800 feet of climbing over rocky trails to the summit of Mount Chocorua. It kicks off the White Mountain Endurance Cup series. Runners must..

A five mile fun run along the Cheshire Rail Trail from the Fitzwilliam Railroad Depot to the restored Troy Depot, with a short children's loop and food and festivities at both depots. The event raises funds for local historical societies.