7 Coziest Small Towns In Maryland

The state of Maryland, on the US east coast, blends history with some of the finest scenery and seascapes of the Mid-Atlantic region. Outside of the state's larger cities, like Frederick and the capital city, Baltimore, the state's true essence may be best considered on a trip through its cozy small towns. Maryland's history and culture will satisfy any high-minded traveler, while those seeking fresh air and natural beauty will also not be disappointed. These Maryland small towns show the best places to look. 

Crisfield

The town of Crisfield, population 2,400, sits on the Tangier Sound inside the larger Chesapeake Bay. Referred to by locals as the "Seafood Capital of the World," Crisfield was established as a fishing village and remains a hub for fishing and seafood packaging today. Fun fact: many locals insist the downtown was built on a foundation of crushed oyster shells. A popular tourist destination, Crisfield offers seafood lovers a chance to sample Chesapeake's best: from fresh crab and lobsters to mussels, clams, and fish of all kinds, the hungry traveler will go home satisfied (and stuffed). Nature lovers should seek out Janes Island State Park, where close encounters with wildlife will create lasting travel memories.

Chestertown

Located on the banks of the Chester River, Chestertown, with 5,600 inhabitants, is a historic town celebrated for its colonial architecture. Strolling through town, tourists can see well-preserved Georgian and Federal-style homes, browse art galleries, and enjoy waterfront dining at Rolph's Wharf sandbar. Visitors wanting more local intelligence should consult the town's newspaper, called the Chestertown Spy. The town's rich maritime heritage is celebrated during the annual Chestertown Tea Party Festival, a lively event commemorating the local resistance to British taxation in the 18th century. Chestertown's small-town charm, welcoming community, and cultural offerings make it a must-visit in Maryland.

Havre de Grace

Havre de Grace, population 15,000, sits on the Susquehanna River at the head of the Chesapeake Bay. The town's very name (from the French phrase "Haven of Grace") reflects the state's unique religious history: Maryland's founder, George Calvert, was himself a convert to Catholicism and wanted to found his colony in part to provide refuge to persecuted Catholics from England and other parts of Europe. Modern, non-religious travelers have just as many reasons to visit here. The lovely Havre de Grace Promenade is a seaside boardwalk that appeals to all seasons. The Concord Point Lighthouse, built in 1827, is another great place to visit and is included on the National Register of Historic Places. Amateurs of history should seek out the Spencer Silver Mansion, which brings guests back to the 19th century in a charming antiquated atmosphere.

Essex

With about 41,000 inhabitants, the coastal town of Essex is among the larger places on this list. And for good reason: locals enjoy living on the Chesapeake Bay while staying close to Baltimore, which lies a few miles to the west. Essex developed in the early 20th century as a calmer alternative to the urban life of the nearby capital city. The town itself sits between the Back River and the Middle River, making its location ideal for water sports and boating. Visitors to Essex can see the Ballestone-Stansbury House, also called the Ballestone Manor. The house, first built in 1800, joined the National Register of Historic Places in 1975. 

St. Michaels

St. Michaels, with 1,100 residents, is a town both small and classy. Yet its upscale reputation provides fun and fascination at all budget levels, given its shipbuilding traditions from the town's founding in 1778. Traveling families might enjoy the 1879 Hooper Straight Lighthouse, a point of interest for all ages. Unique stores line Talbot Street, ready for shoppers and window shoppers alike. Students of local history and industry should head for the Chesapeake Bay Maritime Museum, which features an 18-acre waterfront, a marina, and outdoor and indoor exhibitions. For those who appreciate fine historic homes, St. Michaels' downtown offers examples of Italianate, Federal, and Gothic Revival building styles. The town's historic district has been a part of the National Register of Historic Places since 1986. 

Berlin

Berlin, population 5,300, was founded in 1868 in the aftermath of the Civil War. Though the name sounds like a nod to the German capital city, the town name's actual origin stems from the old "Burleigh Inn," a tavern at a crossroads that developed into modern Berlin. For today's travelers, Main Street boasts an assortment of historic shops and buildings, including the Calvin B. Taylor House, built in 1832. Berlin is a popular spot for hunting and fishing, while a visit to the nearby Assateague State Park on the Assateague Island charms tourists with natural vistas and the background of the local Assateague Horse, a breed of wild animals descended from European colonists. Similar horses also inhabit nearby Chincoteague Island, Virginia. The two islands neighbor one another as barrier landforms by the Atlantic Ocean.  

Chesapeake City

Chesapeake City (actually a very small town, with just 700 residents) sits in Maryland's northeast corner, on the Chesapeake Bay. The town is on the National Register of Historic Places as it bridges the bay and the Delaware River, where it operated a historically important commercial canal built in 1829. The town sits just west of the vertical Maryland-Delaware border that divides the Delmarva Peninsula. Most of the town's 19th-century architecture still stands, and visitors can also enjoy dining, shopping, and seaside strolls. The town offers a good number of bed and breakfasts for its many tourists passing through. Interesting fact: the town's Ukrainian community, present here for over a century, is still visible today, notably at gathering places like St. Basil's Ukrainian Church south of town. 

Maryland's Small Towns Are Worth Several Trips

Given how much charm and interest Maryland's small towns offer, it is little wonder that the state runs a brisk tourism industry to welcome visitors from near and far. Many tourists feel drawn to the state's waterside attractions — indeed, the Atlantic Ocean and the Chesapeake Bay helped establish the former British colony's success. Crisfield and Berlin shine a light on Maryland's past and present fishing industries, while Havre de Grace and Chesapeake City offer clues to Maryland's religious roots. Quaint, cozy, historic, and beautiful: with all that Maryland's small towns have to offer, the state may be the next destination for many travelers' next visits — and for many repeat visits in the future.