The Heart And Soul Of Maryland Is The Small Towns And These 7 Have The Best Downtown Areas

Small-town living is nice, especially when it includes a charming downtown area. These small towns in Maryland always have something going on, including farmers’ markets, car shows, and so much more. And of course, don’t forget the local small businesses and restaurants as well. Read on to learn more about the best downtown areas in Maryland, and be sure to visit every single one when you can!

What other small towns in Maryland with adorable downtowns would you add to the list? Let us know in the comments!

Oh, and speaking of amazing, did you know that St. Michaels was recently named one of the most beautiful towns in America?

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Small Towns in Maryland

September 19, 2022

What are some of the best small towns in Maryland? 

Life in Maryland is scenic and peaceful, and there are all kinds of delightful small towns in Maryland that are worth a look-see. Some of our favorite small Maryland towns include little jewels like Ellicott City, which is a fascinating historic town founded in the early 1770s and perfect for the history lover in your family or friends' group. 45 minutes from Baltimore is a small town known as Bel Air, which is home to some wonderful mom-and-pop shops and eateries you won’t find anywhere else. If you’re a wine lover, you won’t want to miss a trip to Mount Airy, which is home to some of the best wineries in Maryland. 

Where are the small towns in Maryland worth visiting?  

The list of wonderful small towns in Maryland goes on – and it goes on forever! More of our hands-down favorite small towns in Maryland include places like Oakland, which is an awesome town for nature lovers, Berlin, which has a postcard-perfect Main Street you’ll never forget (see more about those in a moment), Monkton (a perfect escape for those looking for something quiet and rural), Hampstead, Eastport, Thurmont, and many more. These are all excellent starting points, however, and we think you’ll enjoy a small-town Maryland road trip or two.  

Where are the best small-town downtowns in Maryland? 

There are lots of small towns in Maryland with wonderful Main Streets, and we think you ought to add each of them to your bucket list ASAP. There’s the above-mentioned Berlin, whose downtown is adorable, but then there are more, like Frederick, which loves going all-out for the holidays, Chestertown, which is definitely one of our favorite fall destinations in Maryland, and Sykesville, which has quite literally been called “America’s coolest small town” more than once.