Unlike the more typical 18th century grid-pattern town planning, Braddock laid St. Michaels out around a central square.

A rural Anglican church that long predated the town gave St. Michaels its name.

For example, Thomas L. Haddaway launched the schooner Lottery at St. Michaels in 1812, and its owners obtained a letter of marque allowing it to take prizes at sea.

Under cover of early morning darkness on August 10, 1813, the Battle of St. Michaels commenced as the British sent a landing party ashore just south of the town, and after a brief exchange, neutralized the battery and returned to their boats.

Based on this story, St. Michaels became known as "the town that fooled the British," a nickname selected during the sesquicentennial celebration of the battle in 1963.

As a means of marketing crabmeat, owner Frederick Jewett devised a five level grading system (regular, claw, special, backfin, and lump) which is still used by the industry today.

The village is a tourist attraction, and there are high quality hotels, inns, seafood restaurants, and gift shops in town.

A for-pay public ferryboat service in nearby Bellevue also takes people across the Tred Avon river to Oxford.

The impetus started with a maritime museum, which opened its doors in 1965, and a waterfront seafood restaurant and a tour boat (the Patriot) followed before the end of the decade.

Major employers include Harbortowne Resort, The Crab Claw restaurant, and the Inn at Perry Cabin by Belmond.

Maryland Route 33 is the only state highway serving the town, connecting it to Tilghman Island and Easton.

In 2007 the town was named #8 of the Top Ten Romantic Escapes in the USA by Coastal Living Magazine.

[11] In 2018 Forbes published an article declaring St. Michaels as "The East Coast Weekend Getaway You've Been Missing".

[12] From April to November, the town hosts a Saturday farmer's market featuring local produce from around the region.

[13] One of the town's chief attractions is the Chesapeake Bay Maritime Museum, located on land that was formerly occupied by seafood packing houses and a cannery.

The Saint Michaels Mill is a 19th century gristmill and was added to the U.S. National Register of Historical Places in 1982.