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James Braddock, an agent for a Liverpool firm of merchants, began developing the town in 1778 by purchasing land grant properties sold at auction. The development area extended from Church Creek (now St. Michaels Harbor) westward to Market Street (now Talbot) and included the inlet known as Church Cove. The planners of the town made an attempt at civic design in the creation of St. Mary's Square where Braddock donated parts of lots to be used for the erection of a Methodist Church.

St. Michaels, named for the Archangel St. Michael, has been an active port in Maryland since the town was developed. A major part of the economy has been based on its shipbuilding industry which specialized in seagoing vessels and bay craft. Log canoes built in St. Michaels and used as workboats in the 1800s evolved into the sport of log canoe racing later in the century. Steamboats, some accommodating up to 2,500 passengers, brought excursionists to Navy Point Wharf in the late 1800s and into the 1900s. Business activity in St. Michaels in the first quarter of the 20th century centered around oyster and crab packing houses and tomato canneries. Today, tourism is a big draw to this picturesque port town where vessels from all over the world visit. The world-class Chesapeake Bay Maritime Museum captures the history of life on this beautiful estuary.

St. Michaels architecture is mainly from the Victorian period, but there are houses on the Walking Tour which date back to the 18th and early 19th centuries. Many of the shops on Talbot Street are historic houses which have been converted into businesses. Walking Tour brochures can be obtained in many of the businesses throughout the town.

By roaming the streets and alleys in this colorful and lively town, history buffs can learn about "the town that fooled the British," Chesapeake Bay watermen, Frederick Douglass and period vernacular architecture.

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