Princess Anne was named for the 24-year-old daughter of King George II. It was established in 1733 and serves as the county seat for Somerset County. Twenty- five acres of “Beckford” Plantation were purchased and divided into thirty lots on a grid plan to form the Town.

In the mid-18th century, Princess Anne gained considerable importance as a market center because of the river trade and the southward extension of the 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 150 acres of the old town are on the National Register of Historic Places.  The present courthouse is one of the most architecturally distinguished in the state. Within the historic district are a few pre-Revolutionary structures, a high concentration of Federal and Victorian architecture buildings, and vernacular dwellings as well as 19th and early-20th century commercial and public buildings. The historic district contains approximately 270 structures of which nearly 90 percent are contributing to the character of the district.

The oldest dwelling in the Town, the William Geddes House (or Tunstall Cottage as it is known to many residents), was constructed around 1755.  The more well-known and significant structures are the Somerset County Courthouse, the Metropolitan United Methodist Church, St. Andrew’s Episcopal Church, Manokin Presbyterian Church, the Washington Inn and Tavern, and the Teackle Mansion. Constructed from 1802 to 1819 by Littleton Dennis Teackle, one of the area’s most influential men of the time, the mansion is the home of the Somerset County Historical Society and is open for tours.