The street has been the main route leading south and west from York from the Roman Eboracum era onwards; the Roman roads to Calcaria (now Tadcaster) and Isurium Brigantum (now Aldborough, North Yorkshire) ran parallel to the modern road, to the rear of the buildings on its north-western side.

Unlike other streets in mediaeval York, it was extremely wide, and as a result, a horse and cattle market was held on it.

By 1639, there were 68 houses on the street, and although there was some damage during the 1644 Siege of York, the presence of a nearby Royalist camp meant it was the only suburb of the city to escape complete destruction.

[2] From the Mediaeval period, the street was known for its inns, mixed with smaller merchants' houses and farmhouses belonging to people who put cows out to pasture on the Knavesmire.

[2][1] Notable buildings on the north-east side include the Windmill Inn, with 17th-century origins; 22-26 Blossom Street, built in 1789 by John Horner, which served for much of the 20th-century as the York Railwaymen's Club; and the Everyman Cinema, designed by Harry Weedon in 1936.