Dogtown Woods in Gloucester, Massachusetts is not your average dog friendly hike. It is an adventure! Comprised of 3,600 acres, the trails wind their way through the abandoned community of Dogtown, past old cellar holes, overgrown apple orchards, and along forgotten rock wall lined roads. In addition, hidden amongst the dense woods are large boulders that were carved centuries later with inspirational mottoes.
This once prosperous community thrived in the mid-1600s. But within a hundred years of settlement soon found itself struggling. Following the American Revolution, wealthy families moved away and were replaced by poorer residents. It was at this time the neighborhood was named "Dogtown" perhaps as a reference to the decline of the community, or for the poor widows who lived there and kept dogs as company and protection. By 1830 the last resident passed away, and Dogtown faded into history. That is until the Great Depression when Roger Babson, founder of Babson College, hired unemployed stonecutters to carve 24 inspirational mottoes on Dogtown boulders.
Today the Babson Boulder Trail and the remnants of the old homesteads, make for an interesting dog friendly hike. Adding to the adventure, the trails are not well marked. Nor are the inspirational boulders easily seen along the main trail. Therefore, maps are available at the trailhead, and are a valuable tool when when exploring the extensive trails at Dogtown. There are also QR codes on signage along the trail to learn more about the former residents and eccentric characters who called Dogtown home.
The trails themselves are overall easy walking, but with some moderate hiking to get over the large boulders that litter the landscape. Be aware though, in order to see all the inspirational boulders, one must cross active railroad tracks and climb a very steep path for dogs. Dogs are allowed off leash, but under voice control.
Parking is available off Cherry Street on Dogtown Road. Look for the sign with trail maps. Then walk past the sportsman club and public works area, until you reach the trail head.