When venturing around the eastern shore, your route may take you through historic Chestertown. This little town has nabbed the hearts of not only locals but many passersby. Read on to see why it’s impossible to drive through this delightful Maryland town without stopping. It just might be the best small town in Maryland!

Chestertown in Maryland was founded in 1706 and still retains much of its historic charm.
Jamie Alvarenga / Only In Your State
The waterfront is lined with an array of visually stunning homes...
Wikimedia Commons / Washingtoncollege
And it's also a gorgeous spot to witness the sunrise.
Flickr / Forsaken Fotos
There are also plenty of things to do in Chestertown. For example, you can head downtown and stroll along the red brick streets.
Flickr / M. G.

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Dozens of shops and boutiques beckon. If you're a fan of the arts, there are also several galleries that will fuel your inner artist.
bpalmer/ iStock / Getty Images Plus via Getty Images
Feeling hungry? Stop by one of the local eateries, including Luisa's Cucina Italiana. Order the cream of crab soup or the cheesesteak. Trust me.
Harold Fink/Google Reviews
If you're in the area on a Saturday morning, swing by the farmers market from 8 a.m. until noon. Here, you can find fresh produce, pottery, crafts, and more.
Town of Chestertown Website
Chestertown is also known for its unique events, bringing the community together in a fun way. Each summer, the town holds the annual Kent County Fair with rides, games, entertainment, animals, food, and all-around family fun!
Kent County Fair / Kent Ag Center/Facebook
Sure, you could drive right by this little town, but why would you want to? It's one of the most charming small towns in Maryland and worth a stop at the very least.
Wikimedia Commons / Jennifer Schmidt

For more information about Chestertown, the best small town in Maryland, visit the official Town of Chestertown website.

Chestertown has a plethora of unique attributes and this article just scratches the surface. What are your favorite things about this Maryland gem?

Visiting Chestertown for a few nights and need a place to stay? Check out The Lodge at Great Oak Landing on Hotels.com, and book your stay!

 

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