If you're like me, the first person to come to mind when you see this name is Winston Churchill, and the first place is Winston-Salem. However, there's a lot more to this name than meets the eye. In fact, it was recorded as far back as 1086 AD in the Domesday Book. Winston is of Old English origin, meaning "joy stone, friend stone" from Wynnstan. (source) Wynn was often used solely in female names. Many baby name blogs and websites confuse the meaning of Winston, claiming it means "wine town," which would only be accurate in Suffolk and Durham, England. (source) Wine meant friend in Old English, (which you can find evidence of in The Wife's Lament, one of the first pieces of literature ever) winn meant joy, and stan meant stone, but in Durham and Suffolk, Wine was a personal name. Such is the case with the Isle of Wight, where the personal name was Wynsige, and Glouchestershire, where it was Wynna. To be clear, Wynnstan came first, and Winston was derived from it, so when the spelling evolved some people changed the meaning from "joy stone" to ">insert personal name depending on location< town." Of course, "friend town," "friend stone," or "friend's stone town" would be more appropriate and acceptable, but "joy stone" would still be the true meaning. (source)Why all the confusion? Because surnames became necessary in old England when personal taxation came into play, known as the Poll Tax. (source)
Wynnstan, long forgotten, would almost be guaranteed to come off as trendy or a "youneek" spelling today. In the Middle Ages it was a place name transferred to use as a surname for those with ties to the area. (source) Such was the case for former British prime minister Sir Winston Churchill, who got the name from the father of his ancestor John Winston, the first Duke of Marlborough. It's also the name of an Australian politician, was John Lennon's middle name, and the name of the main character in George Orwell's novel "1984."
The name ranked on the SSA charts every year since 1883, its highest place in 1940 at #311. (source) In 2011 it was #742, but it isn't obvious if the name is going up or down in popularity. It has also been popular in the West Indies and Caribbean. Winn makes for one excellent nickname, and many people see Winston as a courageous and heroic name because of how valiantly Winston Churchill fought in World War II.