St. Michaels, Maryland

If you‘ve never explored Maryland’s eastern shore, then it’s high time you took a detour on your way to the beach. Just off Route 50 at Easton you’ll bear right and be on your way to the most iconic little town you’ve ever experienced, (and they even have a lighthouse).

#StMichaelsMD is a lovely little town that sits on the Chesapeake Bay and is known for it’s unique shops and small town charm. There is also a fairly large art community and even a winery or two.

I love St. Michaels! My family and I discovered it years ago while we were exploring because we didn’t want vacation to be over. We were on our way home from the beach, had gotten to Easton about noon and the traffic was horrible! I said, “I need to get off this road“ and turned the steering wheel. Next thing you know we are transported back in time to a beautiful, historic downtown with red brick sidewalks and buildings that looked like they fell out of a Norman Rockwell painting. I didn’t want to leave.

According to the town’s history, it was incorporated in 1804 and became a ship building center. Makes sense since it sits on the bay. They‘re known for building a vessel called the Baltimore Clipper. The town was also instrumental in the war of 1812, when the British tried to destroy the ship yard, but failed...

Another historical note about St. Michaels is that Frederick Douglass, a famous abolitionist lived near or in St. Michaels on several occasions as a young child and teenager. When he escaped slavery in Maryland, he became a leader of the abolitionist movement in the mid-1800’s.

We’ve gone to St. Michaels several times since that first fateful frolic and have always found something new to marvel in. The boutique shops that line the downtown historic district are simply fun. My husband found a shop that was made specifically for him the last time we were there.

If you like seafood, then this is the place for you. St. Michaels is known for its fresh oysters that come directly from the bay. Of course you’ll want to grab a steaming pile of Maryland blue crabs and the crab cakes made from these fellows are the best you’ll ever have!

If you’re staying for the weekend you’ll have a bunch of choices from victorian bed and breakfasts to an 18th century Inn. While you’re visiting St. Michaels you can sit and relax with a glass of wine you just purchased from one of the tasting rooms as you’re overlooking the waters of the Chesapeake Bay or if that’s a little slow for you, hop on a kayak, paddle board or hire a fishing guide for the day to catch your prize winner.

Before you go home you need to check out the Chesapeake Bay Maritime Museum at the edge of town. That’s where the opening picture was shot. Here you can tour the Hoopers Strait Lighthouse, see how the skipjacks are built, rent a small craft or book a tour of the scenic waterways in and around St. Michaels.

You need to check this place out! When you do, tell them The Fun Chasers sent you. Cheers!

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