
We’re finally talking about it openly. Portsmouth had a thriving waterfront combat zone in the late nineteenth and early twentieth centuries. In fact, we seem strangely proud of this era with the rise of underbelly walking tours and Red Light exhibitions. City officials and the police knew what was going on, yet the newspaper reported few fines and arrests. Bordello owners paraded their latest sex workers through town in open carriages.
Until 1912, when cleaning up the city’s South End after a series of murders became a political issue, as many as a dozen brothels operated openly. A playing card-sized promotion for a “dance hall” on Four Tree Island shows the sex trade, although technically illegal, was openly advertising its wares.

These two postcards, discovered online, are far from subtle. “We are waiting for you,” two women announce. The first card promotes the I-LONG-FOR-YOU Railroad Company on the True Love Line headed to Portsmouth, NH. The card is signed by the passenger agent named Dan Cupid. Was this an innocently humorous card or a coded message? The back of this card, which was never mailed, includes the pencilled address “644 State” and an indecipherable name.
The second card pokes at the synergy between local police and bordello owners, primarily during the reign of Marshal Thomas Entwistle in the late 19th and early 20th centuries. This colorful image shows a young woman sitting provocatively in the lap of a Victorian-era police officer. The headline reads: Holding Down the Law in Portsmouth, NH.” The officer appears to be gripping his handcuffs while the woman readies his billy club.
Yes, both of these cards were likely reproduced in other cities. The name “Portsmouth” is clearly added in. But the existence of the manufactured card itself speaks volumes for a town, researcher Kimberly Crisp says, was known from Hong Kong to New York for its beautiful women and risqué nightlife. It was the region’s worst-kept secret/
© 2026 J. Dennis Robinson.
SEE ALSO: The bordello on Four Tree Island




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