The Border Reivers were active during a tumultuous period between Scotland and England, spanning approximately 300 years from the late 13th to early 17th century. Reiving, or raiding, occurred on both sides. Each side of the border the land was divided into Marches - east, middle, and west - except for a small sliver known as the debatable lands, which was so lawless that neither side wanted it. The Marches were overseen by wardens, typically local landowners, but in reality, they were often the worst of reivers. Their role was justice and law enforcement amidst frequent border clashes.

A notable Reiving story is the rescue of Kinmont Willie Armstrong in 1596, commemorated in the Great Tapestry of Scotland. He was imprisoned by order of the English Warden, Lord Scrope and held at Carlisle Castle, but was famously rescued by Walter Scott of Buccleuch. Such stories are celebrated in border ballads and the literature of Sir Walter Scott.

Another significant event is the drowning of Reivers at Hawick in July 1562, remembered during the Reivers Festival. Historical records from the National Archives in London document the arrest of 53 men by the Earl of Mar, with 22 being drowned due to a lack of trees for hanging.

The festival highlights key Border family names associated with Reiving, such as Armstrongs, Elliots, and Scotts.