• Explore The Cannonball House. The Federal-style house is a side-hall double-parlor design on a corner lot, built for shipbuilder William Merchant. It is historically notable for an 1813 event in the War of 1812, in which the British fleet bombarded St. Michaels, leaving a cannonball embedded in the house.

• Visit The Talbot Historical Society. From exhibits to educational programs and special events, the Talbot Historical Society is the leading resource for discovering Talbot County's past. The society's museum and historic houses surround award-winning gardens, maintained by the Talbot County Garden Club.

• Travel to the Wye House in nearby Easton. A U.S. National Historic Landmark, the Wye House is among the most authentic Southern plantation homes still standing in Maryland. The renowned abolitionist Frederick Douglass was once a slave on the plantation during his youth and wrote extensively about the experience in his Narrative of the Life of Frederick Douglass, an American Slave.