Up the River – not to be confused with Up the River Without a Paddle, used for an unfortunate situation – is a popular colloquial phrase, applied to describe someone as having been sent to prison.
Originally, it was used specifically for people sent to the Sing-Sing Prison, situated on the Hudson River.
The expression comes from the late 19th century, in reference to the location of the Sing-Sing Prison on the Hudson River, positioned approximately 30 miles north of New York City.
Although its exact origin is not known, one of the earliest uses of the phrase “Up the River” comes from the 1864 publication of Charles Graham Halpine, titled “The Life and Adventures, Songs, Services, and Speeches of Private Miles O’Reilly”.
“Up the River” was soon included in an article of the New York Times, published on August 21st, 1879.
In the following decades, “Up the River” would remain a reference to the Sing-Sing Prison, however, by the 1930’s, it started to gain a much broader sense, used idiomatically for all prisons in American English.
This was largely contributed to by the 1930 comedy film “Up the River”, which inspired several remakes and adaptations over the decades.
The expression was first defined on Urban Dictionary in 2004, with several other entries published on the site since then.