Sure, Maryland is mostly known for its biggest city, Baltimore. But what most people don’t know is that it’s the smaller towns that are the most charming parts of our state. Whether you’re looking to go boutique shopping, grab a coffee, or simply check out historic buildings, Maryland has an array of locations to choose from. Listed below are 10 of the most charismatic and charming small towns in Maryland.

1) Leonardtown
Leonardtown, MD 20650, USA
Elvert Barnes / Flickr
Leonardtown, Maryland offers plenty of history, parks, and downtown shops. It has a variety of things to do while still keeping it perfectly low key. With a population of under 4,000, this wonderfully small town is also a center for the arts as well as entertainment in Southern Maryland. Leonardtown is one of the best small towns to visit in Maryland.
2) Berlin
Berlin, MD 21811, USA
Diane / Flickr
Berlin is a tight-knit community that strives to keep their town looking its best. Located in popular Worchester County, people travel from all over to visit Berlin's delightful Main Street. Enjoy retail shopping, local seafood, antiquing, plenty of nature escapes and so much more in Berlin, Maryland.
3) St. Michaels
Lee Cannon / Flickr
Saint Michaels, Maryland is a town with a small population (just over 1,000). Those lucky enough to call the coastal town home enjoy a picturesque setting. Spend a day on the water, shopping at the boutiques, or learning at the Chesapeake Bay Maritime Museum. This is one of the greatest places to visit and live.
4) Cambridge
cambridge md
m01229 / Flickr
Cambridge, Maryland is one of the oldest established towns in the state. A walk through its historic downtown will delight visitors with gorgeous architecture and friendly people. Cambridge has a vibrant arts scene and plenty of small business's to shop around. Known as one of the best towns in Maryland, Cambridge is a joy to visit!
5) Historic Ellicott City
Ellicott City, MD, USA
Mr.TinDC / Flickr
Ellicott City in Maryland is located just outside of Baltimore. Like many other quaint towns in Maryland, Ellicott City is rich in history. Being situated near two rivers allows for ample outdoor activities as well. Stroll through Main Street or stop by the B & O Railroad Museum, the oldest surviving train station in the country! You'd never know this charming town is right next door to all the big cities.

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6) Havre de Grace
Havre de Grace, Havre De Grace, MD 21078, USA
justgrimes / Flickr
Havre de Grace, Maryland is nestled against the banks of the Susquehanna River at the head of the Chesapeake Bay. This tranquil and beautiful community is named after a port city in France by the same name. With almost 14,000 residents, Havre de Grace is a cultural destination. Check out the Concord Point Lighthouse while touring Havre de Grace as well as the Grace Decoy Museum. The town is also considered one of the best places to live in the state as well as one of the best small towns in Maryland.
7) Vienna
Vienna, MD 21869, USA
Terps Travel / Flickr
Vienna, Maryland has a picture perfect waterfront that is well complemented by its tiny town. The small population of less than 500 makes this town one of the most quaint and quiet places on our list. Find it just southeast of Cambridge. Visitors enjoy Vienna's historical significance as the area was explored back in 1608 by none other than famous Captain John Smith.
8) Boonsboro
boonsboro maryland
Jerry Edmundson / Flickr
Boonsboro, Maryland is a historic town that has several Civil War sites including the Antietam National Battlefield. Check out the many historic sites while staying at the bed and breakfast owned by author Nora Roberts called Inn Boonsboro. Outdoor lovers will enjoy the town's proximity to the Appalachian Trail while travelers like the convenience of Harpers Ferry.
9) Emmitsburg
Emmitsburg, MD 21727, USA
Jon Dawson / Flickr
Located in Frederick County, most of Emmitsburg is rural with old brick buildings and beautiful parks. The town of just over 3,000 people is home to Mount St. Mary's University and has a large Catholic community.
10) Thurmont
Thurmont, MD 21788, USA
Taber Andrew Bain / Flickr
Thurmont, Maryland is known as the gateway to the mountains where you can drive through covered bridges, walk around Main Street, or explore their many parks. Located in northern Maryland, the small town is home to Camp David is a great place for hiking and rural retreats.

Maryland is filled with small and charming towns that are perfect for a visit! From historic sites to shopping and fun, a trip to any one of Maryland’s quaint towns is sure to make for a great stay.

What towns would you add to the list? Share in the comments below.

If you’re looking for jaw-dropping scenery (including wild horses on a pristine beach!) then you MUST see Assateague Island in Maryland.

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small towns in Maryland

Christina Arrascaeta | September 17, 2022

Is Maryland a great place to live?

Located in the Northeastern United States, the state of Maryland is a wonderful place to live. With its top-notch school system, diversity, historical sites, and fresh seafood, Maryland is a popular travel destination as well as a relocation point for many people searching for a great place to live.

What are the best small towns in Maryland?

Outside of Baltimore, Maryland is filled with charming small towns. From Smith Island’s laidback waterside vibe to St. Michaels’ vibrant downtown, visitors are sure to find many great features in Maryland’s small towns.

What are the most beautiful places in Maryland?

One of the best places to experience stunning scenery is the Assateague Island National Seashore on Assateague Island in Maryland. Frolic on 37 miles of pristine beach and see wild horses that call the area home. Another option to see beauty in the state is by visiting one of Maryland’s many state parks.

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