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Supposedly after the wealthy residents moved to the shoreline, the vacated houses of Dogtown became the equivalent of a modern day ghetto, inhabited by societal outcasts and vagrants.
It was during this period in the 18th century that the Dogtown acquired it's name, describing the packs of wild dogs that roamed the area.
Dogtown is too confusing and the beginner will likely find himself lost in a maze of difficult singletrack before too long.
The last resident of Dogtown, a freedman named Cornelius "Black Neil" Finson, was found half-dead living in a cellar-hole in the winter, and was removed to the poorhouse in Gloucester in 1830; he died shortly afterward.
One of the 36 "Babson Boulders" in Dogtown
Dogtown Road off of Cherry Street in the western section (the Gloucester side) is even lined with the remains of the cellar holes of the settlers, many of which are numbered in correspondence with names from John J. Babson's book of the history of Gloucester.