Trail Running Calendar Massachusetts 2025-2026

The Mt. Toby Ultra is a trail running event offering three distance options: 13k, 24k, and 50k, each showcasing the scenic beauty of Mt. Toby.The race serves as a fundraiser for Girls on the Run of Western Massachusetts, promoting joy, health, and confidence among girls through running. Participants..

The Spring Fever 5K | 5M | 8H is a running event taking place on April 12, 2025, at Wompatuck State Park in Hingham, MA. Participants can choose from three distances: a 5K, a 5-mile race, or an 8-hour endurance challenge. The event is designed for all ages and fitness levels, with a focus on communi..

The Merrimack River Trail Race is a USATF sanctioned 10-mile running event taking place on April 12, 2025, in Andover, MA. The race features an out-and-back course starting from the DoubleTree by Hilton Hotel. Participants can register online or on race day, with entry fees varying based on registra..

The 10th Annual F.O.R 5k Trail Race will take place at the McDonald Nature Preserve in Wilbraham, MA. This family-friendly event encourages participants of all ages to enjoy the outdoors while supporting the Recreation Maintenance Fund for local parks. The race features a scenic course rated easy to..

The Tortoise and the Hare Trail Races, scheduled for April 19, 2025, in Salisbury, MA, features a variety of running events including a 10K, 5K, and a 1 Mile Color Run. This family-friendly event aims to raise funds for the Salisbury Parks and Recreation, supporting local park development. Participa..

The TARC Spring Classic, organized by the Trail Animals Running Club, is a trail running event set to take place at the Jericho Town Forest in Weston, Massachusetts, on April 26, 2025. Participants can choose from various distances, including 10K, Half Marathon, Marathon, and 50K. The course feature..

The Radish Rambler 5k at White Barn Farm is a fun and engaging trail run/walk/hike set in the scenic conservation land of Wrentham, Massachusetts. Scheduled for April 26, 2025, this event welcomes participants of all ages and skill levels, marking the opening day of the farm and an Earth Day celebra..

The Cape Cod Trail Race is an exciting running event featuring 10K, 20K, and 30K races, set to take place in April 2025. This event encourages participants to "Run Forward. Give back," highlighting its community spirit and commitment to local support.Registration for the race opens on January 20th,..

The 7 Sisters Trail Race is an exciting running event that features a series of wave starts based on anticipated finish times, ensuring a well-organized experience for participants. Runners are required to carry their own water, as the race is cupless, promoting sustainability. The event is capped a..

The Dandelion Dash and Mushroom Mile is a fun running event taking place in Hadley, MA, featuring a 5K trail run or walk and a 1-mile race suitable for participants of all ages. This event aims to support The Hartsbrook School's unique programming, which includes land stewardship and sustainable pra..

The Watuppa Trail Races is an annual running event held in Fall River, Massachusetts, celebrating its 11th year in 2025. Participants can choose from three race distances: 10K, 30K, and 50K, catering to various skill levels and preferences. The event takes place in the scenic Watuppa Reservation, pr..

The TARC Wapack and Back is a challenging trail running event organized by the Trail Animals Running Club, taking place along the scenic Wapack Trail in Ashburnham, Massachusetts. Participants can choose from three distances: 21.5 miles, 43 miles, and 50 miles, with the course featuring rocky ledges..

The Dash For Dane & Family Day is an annual event held at Powisset Farm in Dover, MA, designed to honor the memory of Dane and support important causes. The event features a 5K Trail Run/Walk, a 1K Kids Fun Run/Walk, and various family-friendly activities such as magic shows, crafts, and live music...

The Tails & Trails State Forest Run, scheduled for May 17, 2025, in Pittsfield, MA, features three race distances: 50K, 25K, and a 5 Miler. This event supports local animal rescue nonprofits, including Red Robin Song Animal Sanctuary, No Paws Left Behind, and Berkshire Bird Paradise, Inc. Participan..

The Trav's Trail Run will take place in Newburyport on Sunday 18 May 2025. You can run between 3 and 3 miles.

The 4K Trail Run is a unique running event taking place in Boston, featuring individual and corporate team registrations. Scheduled for May 21 and 22, 2025, participants can join as individual runners or as part of a corporate team. The event aims to support Boston's youth through fundraising effort..

The Taunton Trail Half Marathon is an exciting running event designed for both beginners and experienced trail runners. Set in the picturesque surroundings of Taunton's waterways, the course is ultra-flat and fast, making it ideal for those looking to achieve personal bests. Participants can enjoy t..

The Powisset Farm Trail Run - Spring is a part of the Barn to Run Trail Race Series, taking place on Memorial Day, May 26, 2025, at Powisset Farm in Dover, MA. Participants can choose from four race distances: 8.3 miles, 5.6 miles, 3.1 miles, and 1.5 miles, all set against the scenic backdrop of Pow..

The Chesterfield Gorge Ultra & 25k is a unique running event held at the Chesterfield Gorge Reservation, featuring a 'choose your own adventure' format. Participants can select from various distances, including 100 miles, 100k, 50 miles, 50k, and 25k, with staggered starts to manage the flow of runn..

The Free to Run Trail Races, organized by the Berkshire Ultra Running Community for Service (BURCS), will take place on June 21, 2025, in Pittsfield State Forest, Massachusetts. This event features three race distances: 15K, 25K, and 50K, designed to challenge participants with scenic trails, long c..