Est. 1728
Click to see a larger version of the mural
Leonardtown courthouse
The Leonardtown Courthouse
circa 1930

Records indicate that by 1654, county court was conducted at the house of John Hammond in the area known as "Newtown" or "Newtowne Hundred".  During the late 17th century, it appears that court was held at various homes throughout Newtown, and that it wasn't until 1708 that an official town with a designated courthouse was established.  It was during this same year that Phillip Lynes, then Mayor of St. Mary's City, Maryland's Colonial Capital, designated fifty

acres of land at the head of "Brittons Bay" to be divided into 100 lots.  He further ordered that one lot be set aside for a county courthouse to be built at an expense not to exceed 12,000 pounds of tobacco.  At this time, Newtown was promptly renamed Seymour Town in honor of Governor John Seymour.  Nearly 20 years later, Seymour Town was renamed again to Leonard Town in honor of Benedict Leonard Calvert, who was Maryland's Governor during this period.  In the decades that followed, Leonard Town became the place where local residents conducted their official business with the colony.


During the War of 1812, the British blockaded the Chesapeake Bay.  This crippled the Tidewater economy and subjected areas such as Leonardtown to repeated British plundering and destruction.  By 1860, the Town had approximately 35 dwellings within these corporate limits.  It was home to the County's newspaper, two hotels and several stores.  During the Civil War, a Union Naval contingent occupied Leonardtown, searching all houses for weapons and supplies intended for shipment across the Potomac to Virginia as Southern Maryland and the Town's sympathies lay with the South.  Leonardtown served as a busy port and steamboat landing until the passing of the steamboat era in the early 1900's.


Leonardtown remains the only incorporated municipality in St. Mary’s County with its own elected Mayor and Town Council. Over the last decade the town has experienced a renaissance with the opening of new restaurants and shops, revitalization of its waterfront as well as several beautifully designed housing developments. In 2013 the Town received a coveted Arts and Entertainment Designation from the State of Maryland offering an even brighter future for years to come.