The People of St. Michaels

The history of St. Michaels, MD, is as rich and captivating as its scenic waterfront views. It's possible that Italian explorer Verrazano may have explored these peninsulas in 1524. Captain John Smith cruised this “delightsome land” during the summer of 1608, marveling at the beauty of the Eastern Shore.

In 1631, William Claiborne, the Virginia Secretary of State and later a pirate (according to Shomette), founded a trading post and settlement just 10 miles from the present-day town of St. Michaels. This trading post, located on the lee side of Kent Island across Eastern Bay, marked the beginnings of a historic community. Approximately 30 years later, the Calvert family, also known as the Lords of Baltimore, supported settlements in Talbot County, named after the sister of Cecilius Calvert, the second Lord Baltimore, and wife of Sir Robert Talbot.

Famous Figures in St. Michaels’ History

The people of Saint Michaels, Maryland, have made significant contributions to history. Frederick Augustus Bailey, later known as Frederick Douglass, one of America’s most famous abolitionists, worked as a slave in and near St. Michaels before escaping to freedom in the 1830s. His story is a testament to resilience and hope, much like the spirit of this historic town.

Notable visitors and residents have graced the town, including Robert E. Lee, who once slept in one of its local homes, and prominent figures such as James Michener, who lived here while writing Chesapeake. The legendary Bill Veeck, known for his influence in baseball, was a resident, and Harold Baines, a famous Major League Baseball player for the Chicago White Sox and Baltimore Orioles, was born in St. Michaels and still calls it home.