PAINT THE TOWN RED
"Paint the Town Red" was extensively discussed in a long article in an
1887 Scientific American (I think), but it doesn't have this, from the
Milwaukee Journal, 29 September 1886, pg. 2, col. 2:
Exciting Origin of a Well-Worn Phrase.
At this late day, says The Pittsburg Dispatch, another origin for the
expression, "Painting it red," is given. Back in the '60s racing was one of
the exciting features of Mississippi river travel, and when an opportunity
offered for a trial of speed all hands were breathless with excitement. The
first command from the captain would be: "Paint her red, boys!" which was
river slang for filling the fire-box with rosin in order to create a quick,
hot fire, at which time the fire-boxes would be thrown open. Then, if the
night were dark, the effect was simply grand. As far ahead as the eye could
see the river would be a deep red from reflection, forming a beautiful
picture, which, once seen, could never be forgotten. It was at that time that
the expression, "Paint the town red," originated, as the old steamboatsmen
intended to convey the idea by its use that they would have a beautiful time
on arrival at their destination.
I gotta go to Toronto. Maybe I'll paint it black.