Jail Bait

How to find one of the nation's oldest jails

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antucket’s Old Gaol, one of the nation’s oldest surviving prison buildings, was very minimum security; prisoners were often allowed to go home at night. You wouldn’t know to look at it. Built in 1806, its massive oak timbers are reinforced with iron straps and bolts that run the width of the walls. Still, there were several escapes, including one of a 15-year-old boy who climbed through the chimney to the roof. He was caught (hey, it’s an island, remember?), and the chimney was rebuilt with a smaller flue.

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The first 20 English families to settle on Nantucket divided the island into 20 equal shares. Tradesmen who came later were give half shares, but ultimately revolted and forced the founding families to accept a democratic form of government in which all property-holding men had equal voting rights.

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