People walking around in Ocean City, Maryland, via Yeilyn Channell /

7 Must-Visit Small Towns in Maryland

Admitted to the Union in 1788, the East Coast state of Maryland is one of America’s most historically rich and geographically beautiful destinations. Also known as the “Old Line State”, Maryland is full of splendid seaside views, fascinating tales of colonial and indigenous history, and plenty of small-town charm. Here, unique Americana can be discovered which in conjunction with the wonderful natural surroundings, make Maryland an absolute treasure to discover. So head on down to these great small towns and see first hand the magic and allure that is the State of Maryland.

St. Mary’s City

Historic St Marys City, Maryland.
Historic St Marys City, Maryland. Image credit Malachi Jacobs via

The first colonial settlement in the State, St. Mary’s City was established in the year 1634 and today it continues to maintain a most special colonial atmosphere that perfectly captures the idea of a living time machine. With a population of just under 1,000 residents (not including the students at St. Mary’s College of Maryland), this humble and historic place is filled with many costumed interpreters, museums, and other important landmarks that will transport any visitor back to the 17th, 18th, and 19th centuries. Explore such sites like the totally reconstructed Colonial Village or the replicated Dove Sailing Ship, which was originally constructed in the 1630s. Add in an assortment of welcoming souvenir shops, tasty locally run eateries, and quiet and calming surroundings, and a trip to St. Mary’s City will surely rank as one of the best outings one can experience in Maryland.

Bel Air

Street view in Bel Air, Maryland
Street view in Bel Air, Maryland, By Famartin - Own work, CC BY-SA 4.0, File:2019-05-21 12 53 16 View north along Maryland State Route 24 (Vietnam Veterans Memorial Highway) just north of U.S. Route 1 Business (Baltimore Pike) in Bel Air, Harford County, Maryland.jpg - Wikimedia Commons

The seat of Harford County, the town of Bel Air was founded in the 1780s where today a population of just under 11,000 residents call home. Once a stop on the famed Underground Railroad network for fugitive slaves, Bel Air is a historically fascinating place full of loads of welcoming small town charm. Explore such places like the Courthouse Historic District, the Graystone Lodge, the Bel Armory, and many other homes that are listed on the National Register of Historic Places. Meanwhile a stroll through Main Street and its welcoming businesses is always a delight, while a tour of a local brewery or two gives guests a unique sampling of some of Maryland’s best locally produced alcohols. And with hot summers and generally mild winters, visiting Bel Air is really a great excursion no matter what time of year.

Mount Airy

Mount Airy Street, Maryland.
Mount Airy Street, Maryland.

Situated at the halfway point between the cities of Baltimore and Washington D.C., the picturesque and rural town of Mount Airy is indeed a most quaint and charming slice of American life. Enjoy the pleasant Main Street where art galleries, cute cafes, boutique stores, and alluring bakery smells all fill the atmosphere, while some great local wineries are the perfect way to discover some of Maryland’s best spirits. And with typically hot summers and mild winters, Mount Airy is indeed a breezy and comfortable place to visit, particularly for those on a road trip to and from the nation’s capital.


Second Street in Oakland, part of the Oakland Historic District
Second Street in Oakland, part of the Oakland Historic District, By Cecouchman - Own work, CC BY-SA 3.0, File:2ndStreet OaklandMD 2589.jpg - Wikimedia Commons

The seat of Garrett County, Oakland was established in the 1860s and today is home to a modest population of just over 1,800 residents. Situated just a few short miles from the beautiful Chesapeake Bay and the Potomac River, this former railroad town is a great place to discover fascinating American history and enjoy the wonders of the outdoors. Spend time at the Historic District where up to 200 unique buildings are listed on the National Register of Historic Places. Including the Garrett County Courthouse (1907), this charming part of town is also full of welcoming businesses that give one a genuine feeling of Americana. Meanwhile the outdoors lover will certainly enjoy spots like the Swallow Falls State Park or the nearby Wisp Ski Resort for great alpine fun!

Havre de Grace

An empty street in Havre De Grace city at dusk.
An empty street in Havre De Grace city at dusk. Image credit Wirestock Creators via Shutterstock.

Just under 15,000 inhabitants call the splendid town of Havre de Grace home which can trace its history back to the 1780s! Stunningly located on the Susquehanna River at the head of Chesapeake Bay, this wonderful seaside destination offers its residents and visitors alike beautiful vistas and loads of historic American stories. Stroll along the peaceful Havre de Grace Promenade, climb to the top of the Concord Point Lighthouse (1827), or explore the Spencer Silver Mansion, amongst many other historic landmarks in this town that will surely leave one with a positive impression. And as waterside settlement, opportunities for sailing and swimming are always popular, while promenade businesses and restaurants all round the unique charm that is this special Maryland town.


City center in Vienna, Maryland
City center in Vienna, Maryland

With a very humble population of nearly 300 residents, the town of Vienna is a quiet and historic community that was founded at the beginning of the 18th century. Surrounded by beautiful green spaces and situated on the shores of the Nanticoke River, the calming ambiance of Vienna is indeed a welcome sight for anyone looking for a break from big city life. Enjoy such activities as swimming, fishing, and even canoeing on the river while an exploration of such historic landmarks like the Webb House (1770), transports one to America prior to its independence. And for the wine connoisseur a trip to Vienna and its area would not be complete without tasting some of the best in local spirits. Stop by the Layton’s Chance Vineyard and Winery where more than 14 acres of land produce delicious and totally memorable drinks for all.

Ocean City

People at Ocean City Boardwalk in Ocean City , Maryland
People at Ocean City Boardwalk in Ocean City , Maryland, via Lissandra Melo /

Although just under 7,000 inhabitants call Ocean City home, this alluring seaside destination welcomes up to 345,000 tourists annually! In a period that can last up to four months beach lovers descend here to enjoy wonderful ocean vistas, hot beach areas, and plenty of intriguing American history from the days of the Thirteen Colonies. Take a stroll along the Ocean City Boardwalk where a fine assortment of restaurants, novelty shops, and many performing musicians and artists all reside. Meanwhile, opportunities to go sailing are always popular, and whether one brings their own vessel or rents, a stunning and picturesque holiday is sure to be had in Ocean City!

The eastern coastal State of Maryland is a great place to discover important American, beautiful natural surroundings, and loads of small town charm. Indeed no matter if one is searching for seaside charm or some fascinating colonial history, Maryland and its small towns are great places for a holiday or perhaps even an extended stay. From the peaceful and picturesque Havre de Grace to the colonial ambience of St. Mary’s City, these and other Maryland towns are always ready to welcome guests of all ages. So wait no longer and come see what makes the “Old Line State” so special!

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