There are plenty of suggestions about the phrase’s origins. Perhaps it’s from Dante’s epic poem The Inferno: "we are they who painted the world scarlet with sins." Or it could be a reference to drinking alcohol – and how people’s faces redden when drunk. Many early mentions are from the Wild West when intoxicated cowboys fired their guns into the air allegedly threatening to ‘paint the town red’ – with blood – if anyone tried to stop them.
The best story, however, comes from Melton Mowbray, Leicestershire in 1837. The notorious troublemaker Henry Beresford, the Marquis of Waterford – known as the ‘Mad Marquis’ – had been out drinking (a bit too much) with friends after going to the races. As the story goes, a toll keeper stopped the inebriated group and they barricaded him in his house. They also stole his red paint.
Rampaging through the town, they splattered the paint on doors and windows throughout the night. When they’d sobered up, the Marquis and his gang were fined £100 each for common assault. An engraving of the event by 19th-century artist Henry Alken, shows the Marquis being hoisted up to paint the sign of the town’s inn, the Swan.
The Marquis’ Melton Mowbray mayhem is a great tale but lacks credibility as the phrase ‘painting the town red’ wasn’t used in reference to him until 50 years later.
It is a gift for the Melton Mowbray tourist office – and we can’t know for sure that it’s not true – but it is likely to have originated in the US. But how, we still don’t know.