Trail Running calendar near Mashpee 2026-2027

A memorial 5k trail run and walk in Kingston, MA on March 14, 2026 that raises funds for a scholarship established by the participant's family. First fifty entries receive a t-shirt and all proceeds support the scholarship.

A Trail Animals trail event at Hale Education in Westwood offering a timed six hour option and a 3.5 mile singleloop on mostly singletrack around ponds. One cupless aid station at start/finish and limited parking with possible walking.

Course and Distance The Run Across CT 123 is a point-to-point ultramarathon that travels coast-to-coast across Connecticut, covering approximately 123 miles (200K). The route passes through 25 towns, starting in East Thompson and finishing..

This USATF-sanctioned 10-mile trail race runs along the Merrimack River in Andover, MA. The event features unique homemade prizes and awards, with proceeds supporting local trail maintenance. Post-race refreshments and a raffle add to the c..

Shake off winter at the Spring Fever trail run in Wompatuck State Park. Choose from a 5K, 5M, or 8-hour ultra on a reversed course. All finishers get a custom award and can enjoy on-course support.

A trail race at Jericho Town Forest (Weston, MA) on April 25, 2026 offering 10K, half, marathon, and 50K options on a marked 10K loop, cupless aid station, strict cutoffs, and parking by volunteers.

Experience three seasons of trail running and walking through scenic conservation land and a working vegetable farm in Wrentham with this unique 5K triple series.

Experience a scenic 5k trail run through conservation land and working farmland in Wrentham. Celebrate Earth Day with an off road course featuring natural obstacles and community focused agriculture support.

Explore the trails at the scenic Frances A. Crane Wildlife Management Area. Choose your challenge with 10K, 20K, or 30K looped courses. This event supports local conservation and community wellness initiatives.

The Watuppa Trail Races offer a fast and flowy course through the scenic Watuppa Reservation. Choose from three distances: a 10K, 30K, or 50K. The event is known for its community feel and welcoming finish line.

Experience the varied landscapes of Block Island with a 10K course featuring coastal tracks and rolling pastures. Running through diverse terrain this spring event includes a steep double tiered climb and views of the Atlantic.

Run a unique 4K trail race on Cathleen Stone Island in Boston Harbor, accessed by a short ferry ride. The two-day event supports free science education for local youth and features a post-race party. Choose to run individually or with a cor..

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..

Run or walk through the scenic Wildcat State Forest Trail in Boxford. This bird friendly event features separate courses for runners and walkers starting at the Danvers YMCA Camp overlooking Stiles Pond.

Experience a timed 5K trail race through the scenic meadows and woods of Coogan Farm in Mystic. Enjoy post race festivities with animal ambassadors and support local environmental conservation at this inaugural event.

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.

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.

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..

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.