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See + Do in St. Michael's, MD

See + Do in St. Michael's, MD

Caroline Ritter
See & Do, United States, Maryland

One of the best weekend trips we take is to the small town of St. Michaels on the Eastern Shore of Maryland. The Inn at Perry Cabin is located there and is a terrific resort made famous when featured in the movie "Wedding Crashers". But this dog-friendly town offers so much more. The shops and restaurants feature local artists, wares and cuisine; you won't find a chain store here. A walk or bike ride through town will also lead you to some fun experiences. Here are my favorites.

  • St. Michaels Winery is absolutely worth a visit. It is in a converted mill, has a lovely little yard and is next door to a cute home wares shop. There is plenty of counter space in the tasting room and with 18 wines to try there is plenty of variety. I LOVE the Sparking Vidal Blanc. No reservation is needed but you can schedule a private or group tasting. Consider this a warning: it's difficult to leave without a bottle of wine to go!
  • Lyon Distilling Co. is another favorite. Founded and run by two sisters, this micro-distillery produces both rum and whisky. The tasting room's warehouse vibe keeps this spot hip and fresh. Ingredients are all locally sourced in Maryland, making it a truly regional product. I left with rum, homemade mixers and a hoodie that I wear ALL THE TIME. 
  • Eastern Shore Brewing is another great spot, located next door to the winery and in front of the distillery.  The beer is brewed on the premises so it's fun to take a little tour - the place isn't big - and follow it up with a tasting. It's a fun and casual vibe!

Chesapeake Bay Maritime Museum is a collection of outbuildings that take visitors through the history of the Chesapeake Bay and eastern shore. One can explore the Hooper Straight Lighthouse, built in 1879 and decorated as it was for its lighthouse keeper at that time.  The view from the top is incredible. The Small Boat Shed shows the process of making small boats, the Waterman Wharf is a working crab shanty and the Maryland Crab Meat Company Exhibition peels the onion on everything it takes to take crab meat to market. My favorite was the Bay History exhibit, which details the Bay's history from before 1612 when John Smith landed in Jamestown. It even displays Native American tools that date back to 8000 BC. Really fascinating and worth a visit.

Whether staying at the Inn at Perry Cabin or not, we always love to visit the hotel's property on a beautiful sunny day. Sitting a spell on one of their many captain's chairs, ordering rose and oysters from the bar and watching the boats come and go all make for perfect relaxing afternoon. For even more relaxation, treat yourself to a treatment in their beautiful spa.

Lastly, walking or biking around the town is always fun. I love to pop into the little shops and support the small business owners.  If you're hungry, please check out my post for restaurant recommendations.

St. Michaels is a great destination, no matter the time of year you visit.