With miles and miles of coastline, a quiet fishing town in Maryland isn’t hard to come by. While most have become a bit modernized through the years, Deal Island is one of the few fishing towns left that remains unspoiled. This serene area almost seems to be frozen in time, and we wouldn’t have it any other way. It’s one of the loveliest small towns in Maryland.

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See Deal Island the way seagulls do:

Have you been to Deal Island, Maryland? If so, let us know about your experiences in the comments. If you visit, just remember to leave no trace behind, so we can continue to enjoy classic Chesapeake Bay gems. For more places to get away from it all, check out these lovely peaceful places in Maryland.

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The Best Towns In Maryland

What are the most charming small towns in Maryland?

The most charming small towns in Maryland include:

  • Leonardtown. This artsy small town has a population of about 4,000 and is full of quaint shops and local history.
  • Berlin. A lovely town with a Main Street that attracts visitors from all over the state. Antiques, seafood, and more await you.
  • Havre de Grace. This is a town that is situated on the Susquehanna River right by the Chesapeake Bay, and the Concord Point Lighthouse is beautiful.
  • Emmitsburg. Come here to see lots of old-fashioned brick buildings and quite a few lovely parks.

Find out more about the most charming small towns in Maryland

What are the best mountain towns in Maryland?

The best mountain towns in Maryland include:

  • Thurmont. This is where you’ll find Catoctin Mountain Park and have a choice of several great hiking trails.
  • New Market. This town is considered the antique capital of Maryland and you’ll also see a plethora of historic homes.
  • Frostburg. It’s an idyllic little college town with some wonderful restaurants well worth checking out.
  • Grantsville. This fairytale town is quite stunning and a complete joy to explore. Don’t miss the historic Casselman Bridge.

Learn more about the best mountain towns in Maryland

What are the most historic towns in Maryland? 

The most historic towns in Maryland include:

  • St. Michaels. You’ll find historic buildings and restaurants and will love exploring all the sights and food available here.
  • Chestertown. Established in 1706, this historic town has historic buildings and historic ships that you can see on the water.
  • Boonsboro. This town has been around since 1792 and boasts a fantastic Civil War museum and often has re-enactments.
  • St. Mary’s City. This was the first colonial settlement in Maryland and you can learn a lot of history in this place.

Discover more about the most historic towns in Maryland