Maryland Just Wouldn't Be The Same Without These 10 Charming Small Towns

For a state on the smaller side, there sure are plenty of worthwhile towns in Maryland. The following 10 spots are among the most charming. With waterside views, historic buildings, and more, these charming small towns in Maryland are always worth a visit.

Saint Michaels, St Michaels, MD 21663, USA

Lee Cannon / Flickr

St. Michaels is full of beautiful water views, plenty of shops, restaurants, and a charming lighthouse. With various bed & breakfasts as well, this is a popular place for a couple's getaway.

Chestertown, MD 21620, USA

Wayne Thume / Flickr

Our favorite thing about Chestertown is the annual Harry Potter themed festival. This area is also home to historic inns and eateries. The atmosphere is peaceful and inviting.

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Oakland, MD 21550, USA

David Brossard / Flickr

Maryland's western-most town makes the list with its railroad history and gorgeous surrounding scenery (and parks). Oakland is home to the multi-day Autumn Glory Festival each year, which is filled with fun events like parades, a craft market, and more.

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Leonardtown, MD 20650, USA

F Delventhal / Flickr

Did you know that Leonardtown is home to the national oyster-shucking championship every year? It's also a family-friendly area with parks and unique restaurants. Come immerse yourself in the charm of Southern Maryland.

North Beach, MD, USA

Ian Gratton / Flickr

North Beach is a bayside town with a beautiful boardwalk, great local businesses, and more. Many people head here for fishing on the bay, as well as relaxing on the beach.

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Havre de Grace, Havre De Grace, MD 21078, USA

Peter Miller / Flickr

This town's Concord Point Lighthouse is one of the most photographed lighthouses in the state. Along with the seeing the lighthouse and strolling along the water, be sure to stop by the local businesses and eateries.

Chesapeake City, MD, USA

Mark S / Flickr

This Maryland town is nestled right along the Chesapeake & Delaware Canal. The charming downtown buildings are home to lovely little businesses and you can also walk across the Chesapeake City Bridge, which will give you an aerial view of the unique town down below.

Berlin, MD 21811, USA

Town of Berlin Maryland / Facebook

Berlin has a friendly small-town feel that draws you in. This community consistently puts on family-fun events and will make you feel right at home. Berlin is a short drive from Assateague Island and other beachy attractions.

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Saint Marys City, St Marys City, MD, USA

Visit St. Mary's MD / Facebook

Learn about Maryland's beginnings at St. Mary's City. This area offers historic landmarks and one of Maryland's best wineries nearby.

Crisfield, MD 21817, USA

Acroterion / Wikimedia Commons

Crisfield is the blue crab capital of the world. Fishermen head here for crabbing and reeling in other local catch. Visit the downtown restaurants, which serve some of the tastiest seafood dishes in the state.

What other charming small towns in Maryland would you add to the list? Let us know in the comments.

Now, how about visiting some more out-of-the-way towns in the Old Line State? Here are 7 small towns in rural Maryland. They’re downright delightful!