Of American-English origin, the colloquial phrase to paint the town red means to enjoy oneself flamboyantly, to go on a boisterous or exuberant spree. The earliest instance that I have found is from Legislative Primer, a satirical dialogue published in The Weekly Register (Point Pleasant, West Virginia) of 18th January 1882:
Papa, what is this?
This, my boy, is a West Virginia Legislator.
Is it alive?
Well, slightly; its [sic] about the liveliest creature you ever saw when it is invited to take a little Mountain Dew.
Well, what is Mountain Dew, papa?
Mountain Dew, my boy, is the liquid representative of a fiery furnace; it is the elixir of a West Virginia Legislator’s life; he would rather do without his dinner than his Mountain Dew, and whenever he wants to paint the town red or paralyze things by making a flowery speech, he gets gloriously full of Mountain Dew.
Do these men paint the town red and make flowery speeches very often?
More frequently than seldom.
The following is from the proceedings of the annual assembly of the Missouri pharmacists, published in the National Druggist (St. Louis, Missouri) of 1st July 1888:
Mr. J. D. Eads, local secretary, who is also mayor of the adjacent town of Warrensburg, was introduced, and in a neat little speech invited the members to enjoy the freedom of the good city over which he presides. He had given the police strict orders in regard to all wearing the blue association badge, and they (the members) need have no fear in wandering around after dark; providing they could find the paint, they might even paint the town red. Considering, however, that Warrensburg is strictly prohibition, there was rather a blue prospect for red paint.
Numerous attempts have been made to explain this phrase. Miscellaneous Literary, Scientific, and Historical Notes, Queries, and Answers, for Teachers, Pupils, Practical and Professional Men (Manchester, New Hampshire) of November 1885 contains the following:
“Paint the town red.” The New York Sun has the following account of this expression:
The origin of the term “painting the town red,” which has been used extensively throughout the State during the last campaign, is attributed to Gov. Thomas M. Waller. Again, it is claimed by Billy Welsh, the minstrel manager, as having been ﬁrst used by his advance man out West, after having literally besmeared a city with big handbills printed in red. When called to an account for wasting the posters, the agent said he was bound to “paint the town red.”
Residents of old Stratford remember Uncle Elnathan Wheeler, who formerly lived up the ferry road. When he was a boy, nearly every other house in town was painted with the old-fashioned mineral red paint, more durable than any that is made nowadays. Having bought a large quantity of the paint at what was considered a low price, Uncle Elnathan tried to induce Harvey Hammond, who lived nearly opposite, to enter into partnership, the two to “paint the town red,” meaning that at the very low ﬁgure nearly every one in town could be induced to “paint up.”
The following explanation is from The Bulletin of the American Iron and Steel Association (Philadelphia, Pennsylvania) of 8th June 1892:
Origin of “Painting the Town Red.”
“How is politics in Harrisburg?” asked Billy Welsh, the minstrel manager, of a reporter. “Red hot,” answered the reporter; “both parties have painted the town red.” Mr. Welsh remarked: “That’s an old expression—painting the town red—do you know where it originated? Well, I’ll tell you. On my last tour through the country with Callendar’s Minstrels, a year ago or more, I had as advance agent a man named Campbell. Campbell was a genius at advertising, and never permitted a rival to get ahead of him. One day in Buffalo I said: ‘Campbell, I hear that Barlow & Wilson are covering my bills with their paper; I want that stopped.’ I told him that he would strike them at Adrian, Mich., and when next I saw him he had huge bundles of bills ready for shipment to Adrian. All were printed in bright red. ‘What are you going to do?’ I asked. ‘I am going up to Adrian to paste these bills over Barlow & Wilson’s and on every dead wall in that place. I am going to paint the town red,’ and he left. When we got to Adrian it looked as if it was on fire, so thoroughly had Campbell done his work. That expression, ‘painting the town red,’ was so comic that the colored minstrels caught on to it, and whenever there was any excitement or anybody got particularly loud they always said somebody was ‘painting the town red.’ Of course it spread, and is now in use by everybody.”—Harrisburg Telegraph.
In Handy-Book of Literary Curiosities (1893 edition), William Shepard Walsh (1854-1919) explained:
Painting it red, in American slang, to go on a reckless debauch, to be wildly extravagant. An outgrowing phrase is “to paint the town red,” or, more simply, “to paint the town.” Originally the metaphor was applied to bonfires, etc., painting the sky or scenery red. Thus, in an old Irish ballad,—
“The beacon hills were painted red
With many a fire that night.”
But the immediate source of the phrase may be traced to the times when a Mississippi steamboat captain would strain every nerve to make his boat defeat a rival. “Paint her red, boys!” would be his command to his men as they heaped fuel upon the roaring fires at night, casting a red glare upon the surrounding scenery. Undoubtedly the phrase was helped into popularity by the fact that to paint—i.e., to paint the nose red—was an old slang term for drinking:
“The muse is dry,
And Pegasus does thirst for Hippocrene,
And fain would paint,—imbibe the vulgar call,—
Or hot, or cold, or long, or short.”
Charles Kingsley: Two Years Ago.
(Two Years Ago was published in 1857. Charles Kingsley (1819-75) was a British novelist, Church of England clergyman and controversialist.)
The first known user of the verb paint in the sense of to drink was the Scottish novelist and poet George John Whyte-Melville (1821-78) in Digby Grand: An Autobiography (1853); the narrator has just met Squire Sauley, “a real Yankee character”:
The day was hot, and my new acquaintance, as he expressed it, ‘a thirsty crittur;’ so each hotel we passed on our pilgrimage called forth the same observation, ‘I guess I shall go in and paint.’ Three times we ‘painted’ accordingly.
The following explanation was published in Notes and Queries (London) of 18th February 1893:
Slang: “Paint the town red.”—
“‘I say,’ suggested George, ‘I have finished my book, and you have nothing to do. Let us pack up our traps and go to Paris and paint the town a vivid scarlet.’ ‘What?’ asked Jonah Wood, to whom slang had always been a mystery. ‘Paint the town red,’ repeated George. ‘In short, have a spree, a lark, a jollification, you and I.’”—‘The Three Fates,’ by F. Marion Crawford, 1892, p. 386.
“To paint the town red” seems generally to be considered modern slang from America; but if Jonah Wood had known his Shakspere [sic] he might have got some light by recalling Prince Henry’s narrative of his friendship with the leash of drawers, of whom he says:—
“They call drinking deep, dying scarlet.”
‘1 Henry IV.,’ II. iv.
Is there anything modern Shakspere did not anticipate?
William George Black.
According to B. A. Phythian in A Concise Dictionary of Phrase and Fable (1993), the most probable origin of the phrase is
an actual piece of drunken vandalism by the Marquis of Waterford and a bunch of his chums who, as an aristocratic joke, actually painted parts of the local town red in the area of Melton Mowbray, Leicestershire, in 1837. The incident created sufficient stir to be recorded in contemporary verse and engraving.
However, it is difficult to explain how an event which took place in England can be the origin of a phrase which appeared in the USA forty-five years later.
Spree at Melton Mowbray.
Larking at the Grantham Toll-Gate.
Or Coming in for the Brush.
A Society of Distinguished Painters,
Who Hunt with Fox Hounds, Live Splendidly and only Paint at Night.
date: unknown – by Henry Thomas Alken (1785-1851)