Book Fair - Origins of phrases

Paint the town red
The origin of this phrase is believed to derived from a a tale dating from 1837. It is said that year is when the Marquis of Waterford and a group of friends ran riot in the Leicestershire town of Melton Mowbray, painting the town's toll-bar and several buildings red. 

Caught red handed
The Red Hand has long been a heraldic and cultural symbol of the northern Irish province of Ulster. One of the many myths as to its origin is the tale of how, in a boat race in which the first to touch the shore of Ulster was to become the province's ruler, one contestant guaranteed his win by cutting off his hand and throwing it to the shore ahead of his rivals. The potency of the symbol remains and is used in the Ulster flag, and as recently as the 1970s a group of Ulster loyalist paramilitaries named themselves the Red Hand Commandos.

Red sky at night, shepherd's delight

The saying is very old and quite likely to have been passed on by word of mouth for some time before it was ever written down. There is a written version in Matthew XVI in the Wyclif Bible, from as early as 1395: 

"The eeuenynge maad, ye seien, It shal be cleer, for the heuene is lijk to reed; and the morwe, To day tempest, for heuen shyneth heuy, or sorwful." 

If we see red clouds in the evening they will be in the east and have already passed us by, giving a good chance of clear skies and fine weather ahead.

Red herring

Red herrings are salted herrings that turn a reddish colour during the smoking process. They have come to be synonymous with the deliberate false trails that are the stock in trade of 'who done it' thrillers.

The term has been used to refer to people as well as to fish for some centuries. John Heywood's 1546 glossary, A dialogue conteinyng the nomber in effect of all the prouerbes in the Englishe tongue includes the expression: 

She is nother fyshe nor fleshe, nor good red hearyng.

In the red

From the practise of using red ink to denote debt or losses on financial balance sheets. Likewise, in the black for businesses that are financially solvent. 

This phrase conjures up images of inky-fingered clerks in Dickensian offices scratching in ledgers with quill pens. In fact, the term is much more recent than that. 

The first known citation of it is in the 1926 Wise-crack dictionary, by George H. Maines and Bruce Grant: 

"In the red, losing money in show parlance."