Have you ever heard the phrase, “the town that fooled the British?” Did you know that said town was actually St. Michaels, MD? That’s right, St. Michaels earned that name during the War of 1812 when residents hoisted lanterns into the trees to fool the British into overshooting the town. Only one house was hit during the attack. This home today is still standing in St. Michaels and is fondly known as The Cannonball House. This is just one of the fun, lesser known facts we learned about the adorable little town of St. Michaels during our recent day trip.

One of the first recorded visits to St Michaels, MD occurred in 1524 when Giovanni da Verrazzano, an Italian explorer, traveled its shores. Then, in 1608, Captain John Smith visited this “delightsome land” in the summer. Another early tale of the town of St Michaels lies in Frederick Douglass. Frederick Douglass became a well-known abolitionist and he actually worked as a slave in St. Michaels before his escape from slavery in the 1830s.

Needless to say, St. Michaels, MD has quite a storied past. Located on the Miles River, St. Michaels transformed into a small village full of shipwrights and other craftsmen helping to support the shipbuilding industry. The local lands proved to be a fertile host to tobacco crops. During the American Revolution, the tobacco industry was moved to the back burner as wheat crops were planted to feed George Washington’s troops. We can then skip to the 1930s when locally owned seafood company Coulbourne and Jewett were shipping out one million pounds of crabmeat and up to 12,000 gallons of oysters per week with the new advancements in steamboats and railroads.

Fast forward to today and the little town of St. Michaels, MD is a charming waterfront destination – well known for its nautical and historical attractions. As we learned on our recent day trip to St. Michaels, the town is home to the lovely and historic Inn at Perry Cabin, the extensive and impressive Chesapeake Bay Maritime Museum, a winery, a distillery, a brewery, an upcoming classic motor museum, and a really cool old mill! Stay tuned for more details on the Old Mill as we were lucky enough to get the tour from none other than its owner, Tad DuPont.

Needless to say, we thoroughly enjoyed Day Trippin’ in St. Michaels. The town also holds a WineFest and BeerFest in the Spring, making it the perfect location for an adults-only getaway. Or, just come to do nothing at all – grab a room at the Inn at Perry Cabin and just enjoy the amazing view for the weekend. Regardless of how you like to spend your weekends, St. Michaels is a town with much to offer. Keep your eyes peeled here for the rest of the tales from our trip and learn just how much there is to love about St. Michaels, MD!