Princess Anne is included in the Salisbury, Maryland-Delaware Metropolitan Statistical Area.
With a population just under 4,000 people, this hamlet at the head of the Manokin River was named for Princess Anne of Great Britain, daughter of King George II. It was established in 1733 and serves as the county seat for Somerset County (the southernmost county in Maryland).
In the mid-18th century, Princess Anne gained considerable importance as a market center because of the river trade. This was later augmented by the southward extension of the Eastern Shore Railroad on Maryland's Eastern Shore. At that time, the Manokin River was navigable as far as the bridge at Princess Anne.
Much of the town's architectural heritage from those days has been preserved. About of the old town, containing about 300 structures, is entered on the National Register of Historic Places as the Princess Anne Historic District.
In addition to the Princess Anne Historic District, the Adams Farm, Beckford, Beverly, Catalpa Farm, Glebe House, Harrington, Manokin Historic District, Manokin Presbyterian Church, Mt. Zion Memorial Church, Dr. William B. Pritchard House, Somerset Academy Archaeological Site, Teackle Mansion, University of Maryland Eastern Shore, Waddy House, Waterloo, and White Hall are listed on the National Register of Historic Places.