7 Playfully Peculiar Towns In Maryland

What happens when a town gets a little too quirky? Maryland lies between the Appalachian foothills and the Chesapeake Bay, with rivers, beaches, and woods all within easy reach. What used to be mostly tobacco plantations and shipping ports is now a collection of commuter cities, Civil War destinations, and quirky roadside attractions. Split between busy metropolitan areas and quiet coastal towns, Maryland hides playfully peculiar places where gold mines are just a gold nugget’s throw from jazz festivals, and rocket gardens sit near co-ops. So if you are itching for a little chaos and curiosity, load up your car, grab your camera, and get ready for seven towns that aren’t like any other.

Berlin

If Berlin had a motto, it’d be “Bring your tub.” One of the strangest events in town happens every June, when the Berlin Bathtub Races send competitors flying down Main Street in wheeled bathtubs. Teams decorate their bathtub-like vehicles, wear wild costumes, and race in front of an ecstatic crowd. The offbeat charm continues at the Mermaid Museum, where exhibits mix ocean folklore with pop culture, beautiful and ancient mermaid art, and plenty of bizarre nautical artifacts.

Just outside town, Assateague Island is famous for its wild swimming ponies, which roam the beaches year-round and swim the channel during the July pony swim. Wrap up your visit with a craft beer at Burley Oak Brewing Company, where rotating taps and homey vibes make the whole place feel like a funky fever dream.

Havre de Grace

If fairy tale towns bore you, this off-kilter gem might be your favorite detour. Start with Dr. Gloom’s Crypt of Curiosities, a collection of creepy oddities including voodoo dolls, Fiji mermaids, and Victorian taxidermy. It began as a traveling show, but is now moving to Havre de Grace as part of the First Call Paranormal & Oddities Museum. Horror filmmaker Chris LaMartina, director of Call Girl of Cthulhu, took over the collection in 2015.

Next is the Havre De Grace Decoy Museum, which displays hundreds of hand-carved duck decoys and celebrates the area’s waterfowl traditions. Steps away, Concord Point Lighthouse, one of the oldest lighthouses on the East Coast, offers breezy riverside views. End with a glass at The Vineyard Wine Bar, where locals sip Maryland wine and snack on small plates in a warm, brick-lined setting.

Hyattsville

This one’s for the creative folks. The standout attraction here is the Vanadu Art House, a private home turned psychedelic sculpture garden, where artist Clarke Bedford welded together a world of chrome animals, machine heads, and surreal car parts. Every September, the town throws the Hyattsville Arts Festival, a full-scale celebration of public art with street installations, local vendors, and live performances.

Relax in Magruder Park, a green space with forest paths, tennis courts, and a few quiet spots to watch the town go by. Then swing by Franklins Restaurant, Brewery & General Store, where you can grab a beer, eat something comforting, and browse quirky gifts you didn’t expect to want.

St. Michaels

This harbor town is known as “The Town That Fooled the British,” thanks to a trick with lanterns in trees during the War of 1812 that caused enemy cannon fire to miss. That resourceful spirit lives on. Start at the Classic Motor Museum, where antique cars and firetrucks sit quietly inside a rustic barn filled with charm and nostalgia.

For a spooky twist, join the St. Michael's Ghost Tour to hear stories of haunted hotels, disappearing brides, and strange lights flickering in the fog. If you time your visit for March, the entire town transforms during St. Michael's ChocolateFest. Restaurants serve chocolate-inspired dishes, bars mix themed cocktails, and shops stock every cocoa creation you can imagine.

Potomac

This isn’t your average suburb; there’s gold in the hills. Head to the Maryland Gold Mine National Historic Landmark, where a forested trail leads past rusted mine shafts and ruins left behind by 19th-century prospectors. It is a strange slice of history in a town better known for its mega-mansions.

Afterward, hike the Billy Goat Trail, where jagged cliffs give panoramic views of the Potomac River crashing below. Once you have worked up an appetite, stop at Old Anglers Inn, a restored tavern with Chesapeake fare. If you are around in July, catch the Potomac Jazz & Seafood Festival, where locals and DC weekenders gather for riverside music and crab feasts.

Greenbelt

This town was created in 1937 as part of Roosevelt’s New Deal, built as a model of cooperative housing during the Great Depression. Begin your day at the NASA Goddard Visitor Center, where full-size rockets launch skyward from the lawn and space exhibits tell decades of exploration history. It is small but mighty.

Then head into Greenbelt Park for a slow walk through the forest, with picnic tables and birdsong far from the main roads. Nearby, the New Deal Café keeps things local with vegetarian meals and a packed live music calendar. In May, don’t miss the Greenbelt Green Man Festival, when art, eco-booths, and drumming circles turn the town into a celebration of earthy weirdness.

Oxon Hill

Where else can you find a giant awakening from the sands but in Oxon Hill? The Awakening is a colossal sculpture of a man bursting from the earth, with feet, fists, and a face scattered across the lawn at National Harbor. Kids climb on it. Adults take selfies.

From there, stroll the boardwalk at Potomac River Waterfront Park, where boats bob in the marina and trails curve around the water. In summer, stay for Movies on the Potomac, a free outdoor movie series under the stars. If you get hungry, book a table at Succotash, a Southern-inspired restaurant where the hush puppies come out hot and the bourbon flows like it’s still Prohibition.

Playfully Peculiar, Dangerously Addictive

Convinced you’ve seen everything Maryland has to offer? You haven’t scratched the surface. These tiny towns have more character than cities ten times their size. One has a chocolate festival. One has a rocket garden. One buries a statue in the sand. Another shows off duck decoys like they’re fine art. Again, these towns are playfully peculiar but dangerously addictive. They are not your normal day-trip destinations. So if you’re tired of predictable trips and want something more human, take the backroads. Slow down. Wander. You might stay longer than you planned.