8 Whimsical Towns to Visit in Maryland
As the “Little America” of the United States, many of Maryland’s attractions and activities are great bite-size experiences of what the country can offer. Colonial-era history, California-like beaches in its Chesapeake Bay area, and quintessential American cuisines (not just burgers) can be found in this Mid-Atlantic region.
However, if you are tired of the usual Maryland hangouts, add something fun and quirky to your next trip! From Chestertown’s Tea Party reenactments to Assateague Island’s shores filled with wild horses, these are not your typical tourist spots. Read on to discover 8 whimsical towns to visit in Maryland that prove that variety is indeed the spice of life.
Chestertown
This little historic port town celebrates its cultural heritage and love for boats through its unique festivals. Believed to have hosted its own “tea party” on the Chester River after Boston’s port closed down, modern-day Chestertown continues this legend by having its yearly tea tossing during Memorial Day weekend with the Chestertown Tea Party Festival. Come November, the Schooner Sultana, which is used for the tea party reenactment, also has its own Downrigging event that gathers Tall Ships and Bluegrass fans for a festival-for-a-cause party.
If that has not captivated your wanderlust heart, perhaps downtown Chestertown’s First Friday might enamor you. It is a monthly event that promotes its art scene and local businesses, like Finishing Touch’s prints and maps and Walnut and Wool’s clothing items, to name a few. For fans of Charles Dickens’s works, make your Christmas extra special with A Dickens of a Christmas event that turns downtown Chestertown into a Victorian holiday. Expect carriage rides, Victorian dresses, and live readings in costume!
Annapolis
Considered one of the most beautiful small towns in Maryland, Annapolis is a popular destination pick for its vibrant downtown, colonial history, and all things nautical! Hit up essential museums like the Annapolis Maritime Museum & Park for a proper maritime history of the Chesapeake Bay, then follow it up with some whimsical fun with Pirate Adventures on the Chesapeake pirate cruises. Your kiddos can search for sunken treasure, fire water cannons, and dress up like a buccaneer!
Like a museum without walls, you will see important statues in the Naval Academy area, such as the Tripoli Monument. Meanwhile, its history-rich downtown has stunning Colonial-era houses that have been turned into beautiful museums for the public—with the Hammond-Harwood House’s preserved 1774 abode and the William Paca House & Garden’s restored 1760s estate as prime examples.
Chesapeake City
Located along the third-busiest shipping canal in the world, Chesapeake City’s modern prosperity and well-preserved old-world charm are a delight to behold. History buffs will get a kick out of C&D Canal Museum’s chronicles and keepsakes of the city’s past. You will find boat models, a water wheel, and even fossils in this free exhibit. Other notable sites are the C&D Canal Museum, which features exhibits on the canal's history, and the Bethel Bridge Lighthouse replica that once guided ships through the canal.
Chesapeake City’s fascination for old things does not stop at canal relics and ships. The town hosts the annual Lion’s Club Car Show, where exhibitors and participants show off their vintage and muscle cars. Usually held in Chesapeake City’s historic downtown area, the city is the perfect venue for a celebration of collectibles from a bygone era.
Assateague Island
With wild horses grazing on sandy shores along the North Atlantic Ocean, Assateague Island near Ocean City is a one-of-a-kind Maryland destination. It is not every day that you get a chance to splash in the waves and play in the sand while horses gallop nearby! The Assateague State Park is the ideal spot for this, but you will need to secure a permit for day use and other activities for a minimal fee.
Other than swimming and kayaking, photographing these majestic creatures is a favorite activity for many visitors. You can also register for Ranger-Guided Programs for a hands-on experience on how to care for this special barrier island habitat. There are no lodgings on the island, but camping with tents and vehicles is welcome. Get your watersports gear from Assateague Outfitters Bayside and munch on some sandals and tacos from Five Tides.
Frostburg
Let Frostburg’s historic train and depot whisk you away on a magical trip through the Western Maryland Scenic Railroad. Traveling from Frostburg to Cumberland, witness the breathtaking mountain scenery between the towns as you ride one of the largest still-operating steam locomotives. You will do more than just sightseeing since the train offers 3-course-meal dinner parties, brewery tours, murder mysteries, and even thematic trips according to the season. Fancy a Polar Express ride this Christmas?
Once you are back in town, Frostburg also has other activities to satiate your whimsical side. Pedal your way through the Great Allegheny Passage with Tracks and Yaks’s rail bike excursions. Travel back in time and learn about Frostburg’s founding with The Frostburg Museum. Love old-timey vehicles? You will have a blast with the Thrasher Carriage Museum and its collection of horse-drawn transports!
Oxford
From its antiquated inn to old-fashioned passenger boats, you might feel like time has stood still in the charming old town of Oxford. It is home to the Robert Morris Inn, a 300-year-old inn that is one of America’s oldest full-service inns. During its prime, some of the country’s Founding Fathers have even slept under its roof. A little ways from the inn is the Oxford-Bellevue Ferry, the oldest privately owned passenger service that takes you on a cruise down the Tred Avon River.
If you cannot get enough of Oxford's history, the Oxford Museum and the Water’s Edge Museum are excellent spots to visit to see America’s evolution and rocky past. After your history-filled tour, a walk through Oxford’s neighborhood will show you the creative painted picket fences around town—a new (and highly endearing) tradition made possible by local artists. Grab a sweet treat from the family-operated Scottish Highland Creamery to cool off from your exhilarating exercise.
Berlin
Amassing accolades over the years, such as Best Town for Shopping by USA Today (2018, 2020) and having been included in the Top 10 Great American Main Street list, Berlin’s historical Main Street is the ideal destination for downtown explorers. Simply follow the red brick buildings and meander through Berlin Commercial District’s 60+ shops housed in 19th-century buildings. Some downtown samples include the retro American diner of Rayne’s Reef, the Victorian-era Atlantic Hotel, and the adorable store of The Church Mouse Thrift Shop.
Perhaps the most whimsical of all Maryland attractions listed so far has to be Berlin’s The Mermaid Museum. Learn about mermaid myths from other cultures, see curious and “haunted” relics, and have a fun photoshoot to live out your mermaid dreams. If you lean more on the hilarious and quirky side, Berlin’s annual Bathtub Races will tickle you silly!
Havre De Grace
Just like the many port towns along the Chesapeake Bay, Havre de Grace has a lot of waterfront activities and attractions—with the Concord Point Lighthouse as the prominent example. However, Havre de Grace edges out other towns for having truly distinctive, whimsy-filled events and spots. Let’s Chalk About Art showcases local artists’ chalk-drawing skills. Shock-O-Con is a new annual horror-themed gathering chock-full of spooky yet intriguing things like Vampire Library and Haunted Carnival. Love boat shows? Do not miss out on The Waterfront Festival’s Lighted Boat Parade!
While Havre de Grace’s Maritime Museum provides an excellent opportunity to learn about the town’s nautical history, the Havre De Grace Decoy Museum next door gives a more whimsical experience. Within, tourists find hundreds of carved wooden waterfowls and information on their usefulness and importance to Chesapeake Bay’s history. You will have a duckin’ good time, for sure!
Maryland’s Quirky Side: A Playful Finale
As one of the USA’s earliest colonies, Maryland’s history-rich landscape is dotted with fascinating museums and historic sites. But beyond dusty relics and century-aged displays, Maryland's whimsical side shines through in places like Frostburg’s magical train rides, Assateague Island’s wild equestrian beaches, Annapolis’s pirate adventures, and Berlin’s quirky bathtub races. Next time you’re in the “Free State,” don’t just settle for crab cakes—explore these zany, playful towns and experience Maryland's unique charm!
