10 Of The Most Eccentric Towns In Maryland
Maryland may be small in size, but its historical and cultural influence make it one of the biggest destinations worth visiting. As the birthplace of “The Star-Spangled Banner,” written by Francis Scott Key during the Battle of Fort McHenry, the state has long been tied to American identity. Nicknamed “The Old Line State” for the steadfast Maryland Line troops in the American Revolutionary War, Maryland is home to some of the most loveably quirky towns to visit in the Appalachian foothills and on the serene shores of the Chesapeake Bay. For 2025, those seeking charm, history, and natural beauty should go wandering through cobblestone streets, discovering maritime legacies, and sipping local wine along quiet trails in the most eccentric towns in Maryland.
Saint Michaels
Located along the Miles River, the charming town of Saint Michaels has an eclectic and eccentric mix of attractions that all will adore. Known as “the town that fooled the British,” the town’s residents are said to have hung lanterns in trees during the War of 1812 to trick enemy ships into overshooting their targets. The Cannonball House, oddly enough, continues to show the damage from the British bombardment. According to local legend, a cannonball bounced off the chimney, burst through a window and bounced down the steps, leaving burn marks that exist to this day in. a quirky and bizarre display of the tenacity, ingenuity, and resilience that Saint Michaels displayed in the war.
Furthermore, both the St. Michaels Museum offers exhibits and walking tours, and the Chesapeake Bay Maritime Museum has interactive displays in what was once a seafood packing site and working dock. Saint Michaels is a haven for fishing and boating, with easy access to the Chesapeake Bay and stunning views at every turn. At the Blackwater National Wildlife Refuge you can marvel at eagles, herons, and other birds that call Saint Michaels’ wilderness their home. Oenophiles, meanwhile, can savor regional vintages along the Chesapeake Wine Trail. Lastly, for a relaxing evening in Saint Michael, you can treat yourself to a few nights at the Inn at Perry Cabin or the St. Michaels Harbour Inn, Marina & Spa.
Thurmont
Thurmont is tucked against the Catoctin Mountains and just 55 miles away from Hancock. One of its more interesting attractions is the Blue Blazes Still, a former moonshine site dating back to the days of Prohibition, and elaborating on a quirky slice of history that you can seek out. Additionally, the town’s historic involvement in the American Revolution is on display at Catoctin Furnace, a restored and preserved 18th-century ironworks that supplied ammunition during America’s fight for independence. Visitors will be enamored by the beautiful settings and landscapes of the surrounding Cunningham Falls State Park, home to Maryland’s tallest cascading waterfall.
Close at hand, you can go trekking through Catoctin Mountain Park, a woodland area brimming with serenity and simplicity. For families, the Catoctin Wildlife Preserve and Zoo offers close-up encounters with exotic animals from around the world, including leopards, lemurs, and meerkats. With so many experiences packed into one scenic town, Thurmont is perfect for a weekend getaway into Maryland’s mountain terrain.
Leonardtown
On the tranquil shores of the Potomac River, Leonardtown welcomes visitors from all over, especially from nearby Washington, D.C., which is about 60 miles away. One of the most bizarre things you will find in Leonardtown is Molly Dyer Rock. Legends and folklore speak of the eponymous local who once lived as a mistreated healer accused of witchcraft, and whose handprint you can vaguely see on the rock. Naturally, many of the folks in Leonardtown warn newcomers not to touch the stone lest Molly Dyer gets upset.
To better spend your time in town, people can always go exploring in the Arts & Entertainment District, where galleries and exhibits supported by the St. Mary’s County Arts Council showcase vibrant local talent. Each year, Leonardtown hosts the celebrated Amish Quilt Auction, highlighting the region’s deep connections to Amish and Mennonite communities, whose quilts you can peruse and purchase. Those of you with a desire to go adventuring can take the Butterfly Trail towards a number of blooming gardens and pollinator habitats. Aside from not touching the Molly Dyer Rock, everything else in Leonardtown is within reach for you, your friends, and your family to seek out and enjoy.
Berlin
Just minutes away from both Assateague Island and Ocean City, the small town of Berlin has earned its spot among America’s coolest small towns, thanks to its quirky charm and eccentric attractions. Originally a crossroads town known as “Burleigh Inn” (and no relation to the city of Berlin in Germany), its name has morphed over time, though its hospitality and welcoming atmosphere have remained unchanged. Its most intriguing landmark is undoubtedly the Mermaid Museum, a whimsical and interactive experience dedicated to the mythical mermaid.
Although decidedly more mainstream, Berlin’s downtown boasts over dozens of historic buildings, many lovingly preserved and listed on the National Register of Historic Places. You can dive deeper into the town’s past at the Calvin B. Taylor House Museum with its collection of antiques and memorabilia. Each summer, the town comes out in full force for its beloved Bathtub Races, a curious tradition in which decorated tubs on wheels zoom down Main Street to cheering crowds. Despite not being as gigantic and culturally rich as the great city of Berlin in Germany, the small town of Berlin in Maryland is a one-of-a-kind destination you will not want to miss.
Ocean City
On a long strip of beach and land between the Isle of Wight Bay and the Atlantic Ocean lies Ocean City. What makes this town remarkable is its origin story. A hurricane in 1933 resulted in massive flooding that all but separated the barrier spit from mainland Maryland. The town turned a natural disaster into an opportunity for developement, building jetties to keep the inlet intact and create a harbor. The result is one of the best resort towns in Maryland, attracting hundreds of thousands of visitors with its wooden boardwalks filled with seafood restaurants and shops.
At one end of the famed boardwalk, Trimper Rides has hosted theme-park attractions for decades, including a popular roller coaster and haunted house. Additionally, Jolly Roger at the Pier is another amusement park with classic rides and carnival vibes. The town also hosts a number of festivals throughout the year. Dreamfest honors Dr. Martin Luther King Jr.'s legacy over three days of live music and community building, while Sunfest is one of the largest outdoor festivals in the region. 2025 will also see the first ever Rising Tides Festival in Ocean City, which will feature a wide range of live music and beachside activities.
Havre de Grace
At the confluence of the Susquehanna River and Chesapeake Bay, Havre de Grace is a picture-perfect harbor town where maritime histories and oceanside attractions await. When a town pronounces itself the “Decoy Capital of the World,” you know you're in a place full of unique character and history. Indeed, Havre de Grace houses the impressive Havre de Grace Decoy Museum, where thousands of hand-carved duck decoys are on full display, as well as interactive tours and demonstrations. Here, one can see how the art of carving decoys has evolved, and why waterfowls and other ducks are so important to Havre de Grace.
When venturing along the Promenade, a scenic boardwalk with sweeping bay views, you can find all sorts of seafood restaurants, cafes, and other buildings of interest. Likewise, the stately Concord Point Lighthouse, one of the oldest on the east coast, offers tours on weekends and that also include the Keeper's House Museum and a lovely gift shop. For another enjoyable immersion into the past, you can visit the Susquehanna Museum at the Lock House, which explores the area's role in 19th-century trade along the Lafayette Trail, and for rural heritage, the Steppingstone Farm Museum showcases early American farming techniques and tools.
Frostburg
Less than eight miles from Cumberland, Frostburg sits at the terminus of the Western Maryland Scenic Railroad. Home to Frostburg State University, the town contains a few unconventional landmarks that might pique your interest. Foremost among them is the site of a would-be full-scale replica of Noah's Ark along Highway 68. In 1978, a ministry set out to recreate the biblical boat, but production stalled and the structure remains largely unfinished, though the footprint gives a sense of the ark's size and scope. Tourists and pilgrims flock to see it every year and the ministry continues to raise funds for the completion of the project.
If you prefer more tangible artifacts, you can admire a rare and extensive collection of horse-drawn carriages at the Thrasher Carriage Museum, an eccentric little gallery that contains sleighs which the Vanderbilt family used, funeral hearses, and President Theodore Roosevelt’s inauguration coach. You can also be delighted to see the Frostburg Depot, complete with a preserved coal train and other locomotives from the past. It is also the ticketing office for a memorable trip aboard the Western Maryland Scenic Railroad.
Crisfield
Founded in 1666, Crisfield is a lovely small town on Tangier Sound, and has been hailed widely as the "Crab Capital of the World." In honor of its honorable title, Crisfield hosts the National Hard Crab Derby, an annual festival that includes crab races, picking contests, a parade, fireworks, and the Miss Crustacean Pageant. Additionally, each summer Big Little Townfest is a community celebration along the scenic waterfront.
Crisfield's Arts and Entertainment District was designated by the state in 2018, and hosts an impressive array of creative spaces, including the Corbin Studio & Gallery. On the other hand, you can hop a ferry to neighboring Smith Island across the Tangier Sound and explore the Martin National Wildlife Refuge. No matter how you choose to experience this town, you will come to adore and admire Crisfield in all its eccentric glory.
Takoma Park
Takoma Park, part of the Washington metropolitan area and thus close to the capital city of the US, is informally dubbed "Azalea City" and has also been designated a US Tree City in recognition of its commitment to effective urban forestry management. Its small-town feel makes Takoma Park a quiet and convenient getaway from much of the surrounding urbanity. One of Takoma Park's most offbeat and iconic institutions is the House of Musical Traditions, a shop that has been selling, renting, and repairing new and used folk instruments from all over the world for more than 50 years.
Even more unusual, however, is The Bird Calls Phone, an art installation in the form of an unconventional payphone that lets you dial and listen to a range of local bird calls. Created in 2016, it went largely unnoticed for nearly a decade, until the Washington Post ran a story about it and the piece went viral. Last but not least, Roscoe the Rooster, a bronze statue located in Old Town, honors a real rooster that wandered the town from 1989 to 1999 and became a beloved mascot until he was ultimately killed in a vehicle collision. Residents commissioned a statue to commemorate their beloved bird, and continue to celebrate his memory by dressing up the statue in holiday-themed costumes throughout the year.
Boonsboro
One of the most quintessential towns in Maryland, Boonsboro is as quaint as it is quirky. One of its greatest claims to fame is that it is the home of famous romance novelist Nora Roberts, whose Inn BoonsBoro Trilogy was set in the town, and which draws a steady stream of tourists and lit lovers to the region on a regular basis. As a matter of fact, fans of the books and those curious to meet Nora Roberts can actually visit the real Inn BoonsBoro, which the author owns with her husband.
Boonsboro is also a popular gateway to the Crystal Grottoes Caverns, with their brightly-lit caves packed with stalagmite and stalactite formations that rival the world's most famous and impressive. The National Road Museum, on the other hand, shines a spotlight on the importance of the very first steps towards connecting the country vis-a-vis the historic roadway. Last but not least, you can take a trip through the past at the nearby Antietam National Battlefield, a historic landmark from the American Civil War complete with interpretive programs and featured tours of the grounds.
Hailed as both “The Free State” and “America in Miniature,” Maryland offers an impressive variety of landscapes and small towns in its biodiverse region. From the birdwatching shores of Havre de Grace to the mountain shadows of Cumberland, and from Berlin’s quirky traditions to Leonardtown’s artistic soul, these eccentric towns in Maryland are reflections of the American experience. Packed with history, culture, and natural beauty, you will come away from these destinations feeling refreshed, enlightened, and inspired to see more of what Maryland has to offer.
