Roland was an 8th-century military commander, serving under Charlemagne, who was killed by the Basques at the Battle of Roncevaux. His name was recorded in Latin as Hruodlandus. His tale was greatly embellished in the 11th-century French epic La Chanson de Roland, in which he is a nephew of Charlemagne killed after being ambushed by the Saracens. The Normans introduced the name to England.
A city in Italy bears this name, though in this case it originates from Latin Mediolanum, perhaps ultimately of Celtic origin meaning "middle of the plain". In some cases the city name may be an influence on the use of the given name.
In the English-speaking world this name has been occasionally given since the early 20th century. It started rising in America after the variant Lorelai was used for the main character (and her daughter, nicknamed Rory) on the television series Gilmore Girls (2000-2007).