The Southend is one of the original medieval streets of Ledbury. Its name, recorded from at least 1288, refers to its position at the south end of the town, on the approach from Gloucester. As often on approach roads, there have been a number of public houses and inns on this street, although now only the Royal Oak remains. Originally laid out with burgage plots on both east and west, it is now mainly built up on the west. The east is bounded by Ledbury Park. The mansion of the same name is at the north east corner, at Upper Cross. The Ledbury Turnpike Trust had a toll gate on the Southend, near Gloucester House. Buildings on the Southend include: The Cookery School (Elizabeth Hall School), The Royal Oak, Gloucester House, and the Southend Toll House.
Content generated during research for two paperback books 'Ledbury: A Market Town and its Tudor Heritage' (ISBN 13 : 978-1-86077-598-7) and 'Ledbury: People and Parish before the Reformation' (ISBN 13 : 978-1-86077-614-4) for the England's Past for Everyone series