In the original 1986 nomination form, the Saint Michaels Historic District consisted of 362 buildings, sites, and structures.

Many of the structures were originally constructed in the 19th century, and used the Federal, Gothic Revival, or Italianate architectural styles.

The Chesapeake Maritime Museum is located along the Miles River and St. Michaels Harbor, in the northeast corner of the Historic District and further north.

[Note 1] Boaters can get to the town's St. Michaels Harbor from nearby rivers or the Chesapeake Bay.

The town's Historic District is lined with shops and restaurants usually housed in well-preserved 19th century architecture.

[4] The Saint Michaels Historic District is located in the center of town, and was added to the National Register on September 11, 1986.

[5] The community that became Saint Michaels began in the mid-1600s as a trading post for tobacco farmers and trappers who took advantage of the deep–water port's access to the Chesapeake Bay.

[6] The church's location meant that it could easily be reached by boat, which was convenient for the early settlers who typically lived along the banks of area creeks and coves.

[7] A list of baptisms dating from 1672 to 1704 includes family names such as Arnett, Auld, Banning, Benson, Blades, Dawson, Harrison, Kemp, Merchant, and others.

The harbor of Saint Michaels became a place large English vessels brought goods for trade.

[10] He had a surveyor measure a portion of his land into lots that were sold, including what became the town's public square.

[14] In 1804, community members petitioned the General Assembly of the state for a charter for a corporate town named Saint Michaels.

[15] Robert Dodson, John Dorgan, James Boid, and Thomas S. Haddaway were the town's original commissioners.

[15] The new town's commissioners did not begin to execute their duties until 1807, and William Merchant replaced James Boid.

[14] The Chesapeake Bay, with its access to Baltimore and Washington (via the Potomac River), was a major commercial waterway in the early 1800s—making it an obvious target for the British in their fight against the United States in the War of 1812.

[16][17] Clipper ships, which were fast but could not carry large amounts of cargo, were used for fighting and evading the British.

[19][20] Master builder Thomas Kemp left Saint Michaels in 1803 to start his own shipbuilding business in Baltimore.

[21] When an economic recession happened after the war, Kemp moved back to his Wade's Point farm near Saint Michaels.

[36] In 1902, African Americans William Coulbourne and Frederick Jewett began a seafood packing house on Navy Point that operated until 1962.

Open on weekends, it focuses on 19th century Saint Michaels, and conducts walking tours of the Historic District every Saturday.

[40] In the original 1986 nomination form, the St. Michaels Historic District consisted of 362 buildings, sites, and structures.

The district is described as "a cohesive group of residential, commercial, and ecclesiastical buildings dating from the late 18th through early 20th centuries located within St. Michaels, a small town fronting the Miles River in western Talbot County, Maryland.