Sir John A. Macdonald, the first Prime Minister of Canada, was born and grew up in the area on and around Prince Edward County in Ontario. One of the most notable historic sites in Picton is its courthouse. The land for the courthouse was donated by Reverend William Macaulay in 1832, a year after a new judicial district was established in the country. Macdonald was indicted for assault when one of his practical jokes went wrong, but he defended himself in this very courthouse where he practiced law.

Macaulay is a prominent local figure who had favour with the Crown. He was granted 400 acres of land in Picton and was educated at Oxford University. He not only provided the land for the court house, but also financed the construction of the St. Mary Magdalene Church where he served as a religious leader. The settlement on the island resulting from Macaulay’s influence is now known as Picton.

Another prominent landmark near the edge of town is the Crystal Palace. It was built in 1887 and modelled after the one at Hyde Park in London, England. It hosted agricultural fairs and others were soon built across the continent. The one standing in Picton is the only surviving structure of its kind in North America and was restored by the provincial and federal governments in the 1990s.