St. Michaels was established in 1778 as a speculative venture by the Liverpool merchant firm of Gildart and Gowith, under the direction of factor James Braddock, who laid out a grid of fifty-eight lots. The plan encompassed St. Mary’s Square, the commercial Market (now Talbot) Street, and the harbor-facing Water Street. Although the post-Revolutionary War period proved disastrous for the company, a sheltered harbor and small affordable lots attracted craftsmen, shipwrights, carpenters, mariners, and watermen, as well as merchants and planters. Principal industries included boatbuilding, oystering, and fishing.
The town’s early-nineteenth-century prosperity is manifested by several Federal-period brick houses such as shipbuilder William Merchant’s house (c. 1810; 200 Mulberry Street). As a working harbor, however, simpler houses built for watermen and craftsmen prevailed, witnessing the development of prototypical forms, such as the Bruff-Mansfield House (c. 1800; 113 Green Street), a one-and-a-half-story, one-room-wide, two-room-deep frame dwelling. The house features a steeply pitched gable roof with a central dormer and a brick end chimney with a partially exposed brick firewall. The two neighboring houses are similarly configured, including the Flemish-bond brick John Harrison House (109 Green). A popular later form is the two-story, front-facing T-plan house with a two-story gallery, exemplified by the elaborate Gingerbread House (1879; 103 S. Talbot Street). It was built for James Watkins, whose name and date are incised in the foundation.
Among St. Michaels’s best preserved and most interesting store buildings is the combination house, store, and office built for real estate agent James Benson (c. 1860–1870; 214 S. Talbot). The store section to the north features intact display windows, and a two-story gallery characteristic of many of the town’s buildings. Other intact storefronts are seen on the former butcher shop (c. 1870), and hardware store (c. 1872) at 308 and 216 S. Talbot, respectively.
Late-nineteenth- and early-twentieth-century industries included seafood packing and canning, while steamboat traffic afforded access to markets in Baltimore and Annapolis for the lucrative oyster trade. Although the harbor now caters mostly to pleasure craft, St. Michaels’s boatbuilding tradition is celebrated by the Chesapeake Bay Maritime Museum, situated in the former industrial area known as Navy Point. Due to its maritime attractions and historic architecture, the town enjoys a vibrant tourist economy.
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