Roger Babson was an author and businessman, who founded Babson College.
During the Depression, he hired men to carve motivational sayings on boulders in some property he owned: Dogtown. A trail which loosely traces through these boulders is a popular destination at the park, and the road/streambed/trail that leads to them is the backbone of the park’s trails. A recently completed map with color-coded trails has made the park’s trail system quite a bit easier to understand, and also incorporated the carved-in-stone, older numbers from a trail system from Babson’s time.
Dogtown is further up Cape Ann than any other trails mentioned here, and perhaps because of that, its sandy soil dries before many other trails in the area.
It is probably for exactly this reason that the place got the name Dogtown! You see, it was once the main settlement of Gloucester (so the story goes), but the residents found it too difficult to farm. The more prosperous moved toward the sea, and the town’s current location. This left behind the less well-to-do the social outcasts, or those who simply preferred to live alone. Since the neighbors were becoming more few and far between, many of the remaining residents kept watchdogs.
As these final residents moved away, passed away, etc., many of these dogs came to be strays, eventually becoming packs of half-wild dogs.
(Nobody has seen any evidence of remaining wild dogs that I’ve ever heard of, but there are quite a few coyotes around MA these days).