Trail Running calendar near Ashburnham 2026-2027

Test your endurance at the Ascutney Mountain Run in Vermont. This 3.7 mile uphill race climbs 2,300 vertical feet along a paved auto road to a scenic mountain summit finish.

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.

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.

Enjoy a 3 mile trail run through the scenic Westport Rivers Vineyard & Winery followed by a vineyard celebration with dinner, wine, and live music.

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.

Celebrate the switch to summer with a trail race through the landscape of Hebron Connecticut. Choose between three different distances for a run through the woods during the solstice.

Run a scenic yet rugged half marathon trail race at Lynn Woods Reservation in Massachusetts. This 13.1-mile event features three challenging loops showcasing the historic Stone Tower. The focus is on sustainability and a centralized start/f..

Experience a 5k obstacle mud run designed for unity and women empowerment at Kimball Farm in Haverhill. Join a supportive community for a day of teamwork and mud while supporting the National Breast Cancer Foundation.

Experience an obstacle course weekend at a lush Massachusetts farm featuring rolling hills and mud. Choose from 5k and 10k races or the kids division with onsite farm treats and a local brewery.

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 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..

Run the TARC Blue Hills Skyline 12K on June 21 in Milton, MA, tackling about 2,300 feet of climbing on rocky, technical Skyline trails. Stair climbs and panoramic Boston skyline views make this a memorable trail challenge.

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.

A unique trail race at Soapstone Mountain featuring six ascents. Runners circle the base and climb each upward trail they find, finishing with the infamous Killer Hill. The challenging course includes rocky and steep terrain.