For a town of its size it has a considerable amount of history connected to it ranging from its ancient connection to crannogs (loch dwellings) to the medieval College Kirk and 16th c. Maybole Castle being the townhouse the Kennedy family and lattterly estate offices in the 20th century. In the 19th century the town was well-known for its boot and shoe industry, with, at its peak, nine factories operating. Maybole is blessed with a highly-informative community website that has been built up over the years and very effectively connects the town to its diaspora.
After a long period of gradual decline the town is now the subject of major regeneration involving schools, shopping and housing.