The Town That Fooled the British

On August 10, 1813, under the cover of darkness and fog, around 300 British soldiers made their way up the Miles River towards a small Maryland town known as St. Michaels.

Upon arriving at the southern end of St. Michaels, they quickly took control of the local militia. Soon afterward, they retreated to their boats and began to bombard the town with their ship cannons.

Now, that part is definitely historical. But what comes next is quite legendary.

Legend has it that the townsfolk hung lanterns in trees further inland, creating the illusion that St. Michaels sat on higher ground, farther from the shore. The British aimed their cannons at the lights — and, well, missed the town altogether.

The same darkness and fog that enabled the British to approach also played a key role in protecting St. Michaels from destruction.

In the end, the British troops withdrew, and miraculously, St. Michaels had no casualties. One house did endure a direct hit from a cannonball, resulting in noticeable damage to its brickwork. Today, that house is referred to as the Cannonball House.

However, there’s a bit of a predicament with this captivating tale: nobody can definitively confirm if the lantern trick ever took place.

Still, this story has woven itself into the very fabric of the town’s identity. St. Michaels proudly identifies as “The Town That Fooled the British,” and you’ll see this claim on the welcome sign as you enter.

A River Town’s History and Industry

Located on the banks of the Miles River, a tributary of the Chesapeake Bay, St. Michaels today enjoys popularity as a summer destination for visitors from Washington, Baltimore, Philadelphia, and even New York. It’s also a prime location for boating and sailing enthusiasts.

Before it became a tourist hotspot, St. Michaels was founded in the mid-1600s as a trading post, attracting trappers and tobacco farmers. An Episcopal parish named after St. Michael the Archangel established the town’s name.

Additionally, St. Michaels developed a bustling shipbuilding industry, particularly known for crafting Baltimore clippers. These ships were celebrated for their speed and agility, ideal for outmaneuvering other vessels and eluding blockades.

This shipbuilding status made St. Michaels a target during the War of 1812. The British attacked the town twice in 1813 as part of their campaign around the Chesapeake Bay. The following year, British forces advanced on Baltimore, bombarding Fort McHenry and inspiring Francis Scott Key to pen “The Star-Spangled Banner.”

As the local economy gradually transitioned toward oyster harvesting and crabbing, the shipyards of St. Michaels continued to produce workboats suited for Chesapeake waters, such as the bugeye—a sailboat commonly used for oyster dredging.

You can still witness this maritime legacy up close.

An Easy Day Trip

Covering only 1.27 square miles, St. Michaels is quite navigable, especially if you’re just stopping by for the day. It’s less than a two-hour drive from Washington, under an hour from Baltimore, and around two and a half hours from Philadelphia.

When visiting, the first place you should check out is the Chesapeake Bay Maritime Museum, which spans 18 acres of waterfront. Given Maryland’s deep ties to the Bay, it’s quite fitting that this is the only museum dedicated to the United States’ largest estuary.

As you enter the welcome center, you’ll come across replicas and original examples of boats used for various activities like racing, fishing, and leisure. The museum also dives into how the bay and its vessels have influenced American history. A highlight is a 23-foot canoe reminiscent of the one used by an enslaved man named Joseph Keene, his pregnant wife Nellie, and their seven children in 1831 as they sought freedom. Keene, an experienced sailor, navigated his family north, likely targeting the newly opened Chesapeake & Delaware Canal and Pennsylvania. Amazingly, they evaded capture and reached safety.

The Chesapeake played a crucial role in the maritime routes of the Underground Railroad, where enslaved individuals navigated the waters to reach northern states, sometimes hiding aboard commercial vessels or escaping on boats. For skilled sailors like Keene, the waterways they had worked on could indeed lead to freedom.

The museum features buildings highlighting various aspects of life on the Chesapeake, from sail making and decoy carving to oyster harvesting. Kids will enjoy the live blue crabs in water tanks, and aspiring watermen can explore a life-sized skipjack or even climb into the pilot house of the Thor, a buyboat from 1912 that collected catches to sell at market.

One of the most impressive aspects of the museum is the opportunity to witness shipwrights restoring and constructing wooden boats. Feel free to ask them anything while you watch.

Additionally, there’s the Hooper Strait Lighthouse, where children can dress as lighthouse keepers before climbing up for splendid views of the water.

Frederick Douglass Lived Here, Too

On the museum grounds, you’ll find the home of Eliza Mitchell, the sister of the renowned abolitionist Frederick Douglass. Eliza lived in St. Michaels with her husband, Peter Mitchell, a free man, until her death. Their originally slated-for-demolition home was moved to the museum in 1981 and is now restored. The Mitchell House provides insight into the life of a family with nine children.

Frederick Douglass himself spent part of his youth nearby while enslaved during the 1830s, working various jobs including as a ship caulker. His experiences here later became significant parts of his narrative about slavery and his eventual escape, and there’s an exhibit across from the museum’s welcome center detailing his life.

The Douglass element adds additional depth to this intriguing town. While St. Michaels is well recognized for its patriotic War of 1812 legend, it also preserves the more complicated history of those who lived along the Chesapeake.

Save Room for Ice Cream

After a few hours at the museum, the perfect way to end your day is to find a cozy spot on the main street for some good food and people-watching.

Talbot Street is the bustling thoroughfare that runs through the historic district, adorned with beautifully restored colonial and 19th-century buildings that house restaurants, antique shops, boutiques, and galleries.

For something sweet, make sure to visit Justine’s Ice Cream Parlour, a local staple since 1987. They boast an impressive “Wall of Shakes” featuring over 90 classic and unique flavors.

If you’re feeling adventurous, try the Titanic Sundae Challenge: over six pounds of ice cream and toppings that must be consumed in less than 30 minutes. “Man v. Food” host Casey Webb succeeded in this challenge in 2019 at the Ocean City location — and you can have a shot at it in St. Michaels, too.

Throughout your visit, you may find yourself reflecting on a remarkable amount of American history packed into a town that’s just shy of a square mile: Chesapeake shipbuilding, the War of 1812, the Underground Railroad, Frederick Douglass, and the generations of watermen who’ve drawn their livelihoods from the Bay.

And who knows? You might even catch yourself wondering if those townsfolk truly did scamper into the trees with lanterns one foggy night in 1813 to outsmart the British Navy.

This question may remain unanswered, but over 200 years later, “The Town That Fooled the British” continues to tell its story.