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In the mid 1700s, the area known as the Commons Settlement was home to Cape Ann’s burgeoning upper crust. As many as 200 people lived in this boulder-strewn flatland until just after the Revolutionary War, when the wealthy moved nearer to the coast. The neighborhood spiraled downward after that, earning the dubious moniker Dogtown; authorities evicted the last holdout in 1830. Walk the dirt road into the old town square, now just a hole-pocked clearing, and bear right at .3 mile to wind past motto-inscribed, glacier-deposited stones on the Babson Boulder Trail. Then wander the 10-plus-mile network of abandoned roads and trails that winds through sparse woodlands. Watch for cellar holes and chiseled exhortations to “get a job” and “stay out of debt” that feel oddly judgmental for a town that couldn’t help itself.
Slurp a bowl of red-and-white clam chowder at Halibut Point in Gloucester. (978) 281-1900
From Gloucester, go north .7 mile on MA 127, right on Poplar, left on Cherry, and right on Dogtown.