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!

1. Havre de Grace
Havre de Grace, Havre De Grace, MD 21078, USA
Facebook / Main Street: Havre de Grace
Shop at the unique stores, chow down at a local eatery, and then stroll along the nearby promenade. This waterside town in Maryland is such a gem!
2. Chestertown
Chestertown, MD 21620, USA
Facebook / Chestertown Arts & Entertainment
Along with great downtown events and shops, Chestertown is also home to many historic buildings, including bed & breakfasts. There's no shortage of places to stay in this lovely little area.
3. Cumberland
Cumberland, MD 21502, USA
Facebook / Visit Cumberland Maryland
Now we move over to western Maryland, where you'll find Cumberland. Grab a hot dog, explore the businesses, and consider also visiting during Christmastime when this area is all decked out in twinkling lights.

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4. Leonardtown
Leonardtown, MD 20650, USA
Facebook / Leonardtown Square
The downtown block of Leonardtown is the perfect space for markets and events. Chow down at the diner and enjoy all the little details that this area has to offer.
5. St. Michaels
Saint Michaels, St Michaels, MD 21663, USA
Facebook / Visit St. Michaels, Maryland
This waterside town has a variety of whimsical boutiques and great seafood restaurants. The town events are full of fun, especially during the holiday season. St. Michaels is known as one of the most walkable towns in Maryland, and we tend to agree.
6. Berlin
Berlin, MD 21811, USA
Facebook / Town of Berlin Maryland
This close-knit community knows how to throw an event! There's always something going on in Berlin, including markets, outdoor movies, and more. Bonus: it's also close to Assateague Island.
7. Sykesville
Sykesville, MD 21784, USA
Facebook / Downtown Sykesville Connection
Last but not least, this central Maryland town has grown into one charming place to shop, eat, and enjoy the farmers market. The festivals are family-friendly and always a good time. Sykesville has literally won "best main street" competitions. You need to go.

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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More to Explore

Small Towns in Maryland

Tori Jane | 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.  

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