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Princess Anne History

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.

The Town is home to the University of Maryland Eastern Shore (UMES). Historically a black land grant college, it now educates approximately 4,300 students each year, with over 400 international students from over 3 dozen countries.


The Town also offers a unique Mobile Phone Tour.  The number is 410.864.7000.  The tour highlights over 300 years of Princess Anne history from the Colonial Era, Revolutionary, Civil and World Wars, the heyday of steam- boat travel, the arrival of the railroad and the first “talking” picture show.  The tour features 68 stories and 40 sites about the people and historic places throughout the Town.

A walking tour of Princess Anne is available here.

Boxwood Gardens

Be sure to see the historic boxwood garden (pictured left) at the intersection of Somerset Avenue and Washington Street. It has been here sine the first half of the nineteenth century. 

The Oaksville Eagles Baseball Team played nearby Princess Anne from 1910 to 1978. The Eagles played against other Negro League teams in the era before desegregation, travelling to neighboring states. At one time they had a 48 game winning streak. Princess Anne Main Street sponsored an exhibit of historic artifacts of the team in three windows of the old PNC bank buildings in 2016 with the assistance of Dr. Kirkwood Hall. Pictured left are photos of the event. More photos are available on the Main Street Facebook Page.


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