The expression, paint the town red, has an interesting origin and the story goes as follows:
One night, a long, long time ago, the Marquis of Waterford had a "jolly good time" in town and was quite inebriated. On his way back to his Castle, where, by the way, the English King signed the Magna Carta, he found a can of red paint. So the story goes. This Marquis thought it would be a wonderful idea to paint all the toll booths between the town and the Castle red. He did, and thus, the expression, "paint the town red."
This was told to us by Lord Tyrone Beresford, the current Marquis of Waterford. We met him at a lavish party in Honolulu. He looked the part of a jolly Irishman with slightly graying red hair and a beautiful, quite young blond. on each arm. They told us that they had just met him at the hotel bar and he was "a lot of fun."
We were invited to this party to have a taste of real old time Hawaii. Beautiful people, gorgeous clothes, lavish food, unending drinks, nonstop music - and all with the Pacific Ocean at the edge of the lush property.