Trail Running calendar near Brattleboro 2026-2027

Two trail races, a new half marathon and a 6k sampler, weave through the scenic Shenipsit State Forest past the Soapstone Mountain tower. The event supports local trail stewardship. A cupless race, it's organized by the nonprofit Shenipsit..

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..

This spring trail run on May 25, 2026, takes you through the scenic paths of Powisset Farm and Noanet Woodlands in Dover, MA. Choose from four distances, from 1.5 to 8.6 miles, in this cupless race. It's part of a farm-based series with awa..

A scenic 2.5 mile off-road run or walk around Horn Pond paired with a festival at Ice House Park featuring food trucks, a DJ, raffles, kids activities, and over 25 local mental health and substance use providers.

Overview The Connecticut Ultra Traverse (CUT) is a point-to-point trail running event with two distances. The CUT112 is a 112 mile run following the Blue Blazes of the New England Trail (NET) from the Massachusetts-Connecticut border to the..

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.

Tackle the infamous "staircase of death" on a rugged 3.8-mile loop in New York. Choose to run solo, join a relay, or take on the flexible Fun Run over a 12-hour period. Start when you like and run as many laps as you can.

Run a flat, out-and-back course on the scenic Holliston Rail Trail. This event offers a 5K and a 10K for adults, plus a fun run for kids with distances based on age. The community gathering point is Blair Square in Holliston.

The Sunapee Scramble is a two-lap mountain race at Mount Sunapee Resort, featuring 9.3 miles and 3,300 feet of climbing. It hosts both the USATF and Collegiate Mountain Running National Championships in 2026. The event also includes the New..

Experience a scenic New England trail event in Dunstable with a 5 mile loop or a 6 hour timed challenge. Support the Humane Society while running through historic quarries and former ski hills.

Explore the hill towns of western Massachusetts on a mix of trails and dirt roads. Choose from a 50k, 30k, or 10k distance, with all proceeds supporting the Franklin Land Trust's conservation efforts at the scenic Edge Hill Conservation Are..

Explore the trails of Mansfield Hollow State Park at the Nipmuck South Trail Race. Choose between a scenic 15 mile out and back route or a new, challenging 5K course. Proceeds support local trail stewardship organizations in Connecticut.

Experience a mountain run at Killington Resort featuring 3,010 feet of vertical gain over 8.2 miles. Runners summit three peaks and tackle a steep 45 percent grade climb before finishing at the K1 base area.

The Rochester 5K Trail Run/Walk is a 4th of July event on marked forest trails. It starts and finishes at River Brook Park, following a loop with single-track sections and rolling hills.

Notchview Ultra features a 1.9-mile groomed loop trail in Windsor, Massachusetts. The event includes multiple ultra distances from 6 to 72 hours and a 100.7-mile race. Proceeds support the Trustees of Reservations and a local humane society..

Gather your team for a two day relay through the scenic Vermont countryside. Run flowy single track trails and camp under the stars at the Ascutney Outdoor Center for an unforgettable weekend of adventure.

The 48th annual Goshen Gallop is a trail run on the tough, scenic paths of the Blueberry Hill Outdoor Center. Runners can choose a 5 km or 10 km distance. All proceeds go directly to maintaining the beautiful trails you run on.

The Spaulding Woods 50K is a technical trail race on a 5.6-mile loop in Northfield, New Hampshire. Runners complete six laps, with 4,400 feet of elevation gain, within a ten-hour limit. The event supports Spaulding Academy & Family Services..

Experience one of America's oldest 100 mile ultramarathons featuring 17,000 feet of climbing through the Green Mountains. This historic event supports Vermont Adaptive Ski and Sports and uniquely includes a concurrent horse race.

Join a community trail run or walk at Owen Bell Park to support the Ryan French Memorial Scholarship Fund. This family friendly event features a 5K trail, a walk, and a free kids fun run.