|The Harrowing of Hell, from|
|a 14th century manuscript.|
The farm implement harrow comes from the thirteenth-century Middle English word harwe / haru, which derives from Old English *hearwa, which is akin to Old Norse herfi / harfr, meaning harrow, and the Dutch word hark, meaning rake. Some suggest it might be connected to the Old English word for harvest hærfest, although a harrow isn't used for harvesting.
So how did we get from farm implement to distressing pain? I could not find a definitive answer. Around 1000, Aelfric, Abbot of Eynsham, used the word harrowing in his homilies when discussing the descent of Christ into Hell to free the righteous during the days between his crucifixion and resurrection. Aelfric termed it the "Harrowing of Hell." William the Conqueror's campaign to lay waste to the northern shires in 1069-70 to prevent future revolts was known as the Harrying or Harrowing of the North. William's soldiers destroyed crops and property as well as slaughtering residents. It was certainly a harrowing experience for the citizens of northern England.
Sometime during the tenth and eleventh centuries, the verb harrow, which can mean to drag a harrow over a field, acquired a meaning similar to the verb harry. Harry means to make war, ravage, or plunder. According to the Anglo-Saxon Chronicle, the Vikings harried England. Harry derives from the Old English word hergian, which comes from the Proto-Germanic *harjon. There are cognates in Old Frisian urheria, Old Norse herja, Old High German herion, and German verheeren, all meaning to plunder or destroy. The meaning of harry has weakened since Anglo-Saxon times. In the fifteenth century it came to mean goading or worrying someone.
And here's a bit of movie trivia to lighten the harrowing mood. Harrow on the Hill, an affluent area of north west London, is home to Harrow School, commonly known as Harrow, one of four all-boy boarding schools in Britain. Among its distinguished alumni are actors Benedict Cumberbatch of Sherlock fame and Cary Elwes, who portrayed Westley in The Princess Bride.