The Town of Princess Anne was established by an act of Maryland's General Assembly in 1733 and named in honor of the daughter of King George II. Located at a narrow point on the Manokin River known as the "wading place," the land was well elevated and favorably suited for the purposes of a centrally located town in Somerset County. Twenty-five acres of David Brown's "Beckford" plantation were purchased and divided into thirty equal lots, with Bridge Street (Somerset Avenue) serving as the main north-south thoroughfare.

The original courthouse was erected on the corner of Bridge and Broad Streets, but the court buildings were relocated to Prince William Street after a fire in 1832. During the prosperity of the nineteenth century, the town was expanded beyond its eighteenth century limits, with new houses erected in every direction. Today, Princess Anne is distinguished by numerous Federal style dwellings, as well as mid-to-late nineteenth century Victorian houses, and turn-of-the-20th century commercial structures.