Dylan in the Details is a travel interested in culture, history, and giving you the best recommendations for your next trip!

Small Town Spotlight: Saint Michaels, Maryland

Small Town Spotlight: Saint Michaels, Maryland

While I love trips to huge cities or faraway lands, I also find myself constantly falling in love with small towns. Whether you’re looking for a weekend trip or a stop on a road trip, Small Town Spotlights is a collection of my favorite hamlets across the country.

One of my absolute favorite weekend getaway spots is the waterfront town of Saint Michaels, on the Eastern Shore of Maryland. Driving over the bridge into town, I feel like I’m crossing into the quintessential fictional town. The magic of Saint Michaels is that time seems to pass only with the lapping ocean waves and everything from friends to dinner is never more than a few blocks away.

(Now, I don’t live in Saint Michaels. As with most things, I’m confident that my limited number of days spent on its shores ensure that the thrilling nature doesn’t fade.)

Besides being gorgeous, Saint Michaels is also famous for its involvement in the War of 1812. Legend has it that the townspeople dimmed their lanterns to fool the British into thinking the town was farther away and thus overshooting their canons. While there is debate about the factual basis of this story, I like to believe it’s true and enjoy the Union Jacks hanging around town.


What to Do

Obviously you can’t come to Saint Michaels and not do some sort of water activity. Whether you want to lounge by the water or boat or kayak or whatever else, you have to enjoy the blue skies and beautiful water. Once you’ve had your fill of the water, you can explore town either by boot or by bicycle. Take in the shops and restaurants and enjoy the local rhythm.


Where to Eat and Drink

Ava’s Pizza

With a cozy interior and a beautiful back porch, there is no bad seat at Ava’s. My recommendation is to grab some drinks and split a pizza, you can’t go wrong with their endless of options for toppings.

Carpenter Street Saloon 

The upstairs bar a C-Street will forever be one of my favorite places to celebrate New Years. I have no perspective on the quality of food, or even the downstairs atmosphere, but I can say that a packed bar on the off-season seems like an indicative rarity, even if it is New Years.


Eastern Shore Brewing

If you like craft beer, then Eastern Shore is the place for you. Located right downtown on Talbot Street, Eastern Shore Brewing is surrounded by plenty of other shops and restaurants. With a website that describes their closing hours with an ‘ish’, you know this is a place where the locals come to hang out.


Great Shoals Cellars

With a great selection of wine and cider, Great Shoals Cellars is the place to come when the heat index is high and you want some air conditioning along with your afternoon activity. Also situated down the street from Eastern Shore Brewing, they made a great pair to satisfy the preferences of the members of any group.

Foxy’s Harbor Grill

If you’re looking for Margaritaville on the Eastern Shore, Foxy’s is your place. Only open part of the year, this place has the umbrellas and faux cabana feel that, after a few drinks, might help you forget that you’re on the bay and not at the ocean. If you can’t get enough of the Foxy vibe, they also serve food.

Rise Up Coffee

After a weekend of walking, socializing, and enjoying the water, you may need a pick-me-up on your way out of town. While it looks like an unsuspecting little kiosk, Rise Up's drive-through offers a wide variety of caffeinated options. The website notes that, while Rise Up is now known across the country, it all started at this little stand in Saint Michaels.


And finally, endless gratitude to Jackie and her family in Saint Michaels, who always welcome me back – no matter what time of year.

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