The original parish of Hawkesbury represented a large and important estate in the hundred of Grumbald’s Ash; it was given to Pershore Abbey early in the medieval period and then passed into secular hands in 1545 after the dissolution of that monastery.

In 1252 the Abbot of Pershore was granted the right to hold a weekly market or fair on his manor at Hawkesbury; this grant seems to have been the spur to the Abbot to lay out a new urban settlement adjacent to the existing hamlet of Upton. This layout is probably the basis of High Street and Park Street, and many buildings along those streets still have long, narrow property boundaries which are typical of new medieval towns.