The establishment of Leonardtown at the head of Britton’s Bay in 1708 occurred after the capital was moved from St. Mary’s City to Annapolis. St. Mary’s City mayor Phillip Lynes laid out a hundred lots, designating one for the construction of a new courthouse. While an active port and steamboat landing, Leonardtown did not experience significant growth until the mid-nineteenth century, facilitated by railroad transport. The early twentieth century was marked by architectural improvement throughout the county, particularly within aspiring towns such as this. Centered around a town square that includes a World War I memorial, most of the buildings date to Leonardtown’s later rise. Notable exceptions are the Old Jail Museum (c. 1858; 41625 Court House Drive) and Tudor Hall (c. 1760s; 41680 Tudor Place).
Of particular note is Mercantile Bank of Southern Maryland (c. 1921, Robert L. Harris, Frainie Brothers & Haigley, builder; 1966 enlarged. 41615 Park Avenue), a handsome Classical Revival building indicative of Leonardtown’s early-twentieth-century prominence. Duke’s Fountain Bar Restaurant (1920s; 41655 Fenwick Street) was erected by Roland Duke as the first reinforced concrete building in southern Maryland. It is distinguished by its modern stepped parapet roofline, casement windows, and painted signage.
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