Maryland has an abundance of small towns that are sure to surprise you. After all, it’s not the size of a town that’s important; it’s the little things like the people, pride, and underrated attractions. The following spot just may be one of the best places in the Old Line State. It’s charming as can be and has a lot to offer. Check it out below!
St. Michaels is located in Maryland’s eastern portion, complete with water views.
It’s on the smaller side, but it packs a lot of punch. There are a multitude of stores that are perfect for a warm-weathered shopping trip.
After all that walking, you’re sure to become hungry. Check out the area restaurants, dessert shops, and cafes to replenish.
A few of the local eateries are right on the water and they offer fresh seafood, from succulent oysters to mouthwatering steamed crabs. Who wouldn’t love this view while chowing down?
If you’re craving something with a kick, head to St. Michaels winery and sample the various wines. Note: Gollywobbler Red is a fan favorite.
You can explore the Maritime Museum and Hooper Strait Lighthouse any time. These spots are even more fun when seasonal events take place.
And speaking of events, don’t miss out on St. Michaels during the holiday season. This town gets really into the festivities with an abundance of fun things to do…
…and the twinkling lights transform this spot into an even more magical place.
There are several area inns for those who want to extend their stay at St. Michaels. Pictured below is the Inn at Perry Cabin, which you may recognize from the movie Wedding Crashers. Although this famous inn is on the pricier side, there are other local accommodations for every budget.
For all of these reasons and more, St. Michaels has become a go-to destination for Marylanders and even out-of-state visitors. If you haven’t checked out this charming place, start planning your trip today.










For more information about St. Michaels, visit the town’s tourism website here.
If you’d like to know about more charming waterside towns in Maryland, click here!

