St. Michaels History and Heritage Itinerary

In 1677 an Episcopal Parish was established on the banks of the Miles River and named after Saint Michael the Archangel. From its early days as a shipbuilding town, its growth as a center for the oystering and crabbing trades and through its late twentieth century transformation into a tourist and sailing haven, St. Michaels and its citizens have forged a way of life that is renowned for its beauty, tranquility and craftsmanship.

The charm of St. Michaels lies in the careful restoration and preservation of the town by citizens who are proud of their heritage. A visitor today can experience a sense of history with a self-guided tour that retraces the steps of those long-ago soldiers and townspeople.

The original street plan was laid out by developer James Braddock in the late 1770s, with lots laid out around a central square. St. Mary’s Square today is the site of the St. Michaels Museum, which is a must-see for any visitor interested in the history of St. Michaels. Among the beautiful historic homes that border St. Mary’s Square is one of the most recognizable structures in the area, a private home known since the War of 1812 as the Cannonball House.  

Early on the morning of August 10, 1813, a number of British barges sailed up the Miles River intending to shell the town and its harbor fort. The citizens of St. Michaels, having been warned in advance of the planned attack, had evacuated most of the women, children, livestock and valuable possessions to an area outside of town known as “Onion Hill.” 

A British landing party came ashore, and the defenders of the small battery at the mouth of the harbor fled into town. The British returned to their boats and shelled the town, while two artillery batteries returned fire from the shore of the harbor. According to local legend, Brigadier General Perry Benson, commanding officer of the Talbot County militia, ordered lanterns placed in treetops just outside of the town and all other lights in the town extinguished, causing the British to overshoot the town. 

Among the few dwellings hit was a brick house near the harbor now known as the “Cannonball House.” Whether true or not, the story inspired the town’s moniker as “The Town That Fooled The British.” The British suffered two wounded men during their brief invasion, and the Americans reported “no injury to any human being.”

Let's Start Your Day!

First Stop: 
Visit St. Michaels Museum at St. Mary's Square as noted above, and walk in the footsteps of soldiers and townspeople who called St. Michaels home centuries ago.  

Second Stop:
Hop on one of the areas boating excursions, from narrated river boat tours, to educational skipjack voyage to a relaxing sailing cruise, you're sure to enjoy your time on the water, and learn about the areas rich nautical history along the way.


Third Stop:
Enjoy lunch at a restaurant of your choice, in town, or along the water, there are many outstanding places to choose, featuring local regional seafood dishes, Italian, Irish, you name it! 

 
Fourth Stop: 
Visit the Chesapeake Bay Maritime Museum, Situated on 18 waterfront acres, featuring the Hooper's Strait Lighthouse at the heart of the complex, the Museum offers exhibits, demonstrations, boat rides on the Miles River, and annual festivals that celebrate Chesapeake Bay culture, boats, seafood, and history. The Museum’s educational programs and resources are designed to bring the vibrant heritage, ecology, and culture of the Chesapeake Bay alive through hands-on experiential learning.  

Fifth Stop: 
Enjoy dinner at a restaurant of your choice, with so many top rated restaurants to choose from, you'll want to stay another day....or two!