"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.