Dogtown 5 Mile Trail Race

Dogtown 5 Mile Trail Race

The Dogtown 5 Mile Trail Race on Sunday, June 07, 2026 is organized by Cape Ann Trail Stewards and takes place in Rockport and Gloucester, MA. The marked course covers approximately 5.4 miles and starts and finishes near the water tower at the top of Summit Ave in Rockport.

Terrain varies along the route. Sections include carriage roads with minor rocks and roots as well as technical stretches with extensive large rocks that require short boulder-hopping. The course passes through several named areas of Dogtown, including the Squam Path, Norton Memorial Forest, Whale's Jaw, the Luce Trail, Briar Swamp, and the Rockport Town Forest.

Parking and meeting are by Evans Field at 3 Station Square in Rockport; participants walk through Evans Field to a trail leading to the registration and check-in area. Signs and event staff will guide participants to the water tower area.

Runners and walkers are both welcome. Walkers start behind runners and use the same marked course. The course remains open with on-course support such as safety monitors and a water stop.

Registration fees are listed for members and non-members with a discounted code option. The first 100 registrants are guaranteed race T-shirts. Prizes are awarded to first overall in each gender and to winners in age groups 39 and under, 40-49, 50-59, 60-69, and 70 plus. The race is part of the 2026 North Shore Trail Series. Visit the organization's website for the most recent information.