St. Michaels, MD

Once a waterman’s enclave, St. Michaels has transformed into an upscale tourist destination, but the town hasn’t lost its quaint flavor. Spas, a brewery and a winery have joined an evolving array of restaurants and inns in historic homes and on the water.

St. Marys Park is the location of one of two cannons commemorating “the town that fooled the British” during the War of 1812. As the story goes the British began shelling St. Michaels on August 10, 1813. Residents boosted lanterns into the tops of trees in order to fool the Redcoats into shooting too high. Evidence of the evening remains at the private Cannonball House on Mulberry St.

This port town was an early shipbuilding center where the swift Baltimore Clippers were built. St. Michaels went on to become a packing house center for seafood and tomatoes (a fine Eastern Shore staple come summer), as well as home to many a waterman. Log canoes, once American Indian transport and now working boats, are famously raced here.

Today St. Michaels is a top destination on the Bay for everyone from boaters to road trippers. If there are any four-legged members of your crew, be sure to take them for some shore leave in St. Michaels. This may be the most pet-friendly town on the East Coast; almost all shops here have water bowls out and many restaurants not only have pet-friendly outdoor seating but have special pet menu items too!

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