8 Fairy-Tale Small Towns In Maryland
Maryland may be small in size, but there is no limit to the amount of charm you can find throughout its modest territory. From the scenic coastline of the Atlantic Ocean to the towering peaks of the Appalachian Mountains, the Old Line State is awash with enticing destinations any traveler would be glad to discover. Venturing outside the popular tourist hubs and major metro areas allows one to encounter delightful under-the-radar towns with a mixed bag of surprises.
Between their gorgeous natural beauty, unique cultural treasures, and well-preserved historic districts, these underrated small towns in Maryland reveal a novel side of the state that only a few get to experience. Whether you are chasing maritime history in Havre de Grace or beachfront splendor in Ocean City, uncover fairy-tale places to see in Maryland.
St. Michaels
St. Michaels is a waterfront gem on Maryland's Eastern Shore, revered for the Victorian architecture that decorates its historic district and the shimmering waters of the Miles River. Its location allows it to have an enduring maritime heritage that the Chesapeake Bay Maritime Museum has extensively documented. A guided tour showcases a curious collection of artifacts, old vessels, relics, and other memorabilia. From the museum, you can spot the conspicuous Hooper Strait Lighthouse, which has been guiding vessels navigating the Hooper Strait since 1879.
Tourists enjoy taking the Patriot Cruises excursion to experience St. Michael's storybook beauty from the water. This easygoing sail lasts about 70 minutes down the calm waters, spoiling guests with vivid views of centuries-old historic mansions along its banks.
Cumberland
Enveloped by the undulating landscapes of the Allegheny Mountains, Cumberland introduces visitors to the unmatched beauty of Maryland's western mountain towns. Its forested surroundings are best pronounced in the fall as the leaves change color, and riding the Western Maryland Scenic Railway presents front-row vistas of the fairytale scene. Meanwhile, the town boasts a walkable downtown district that stirs nostalgia with its historical landmarks. The Gordon-Roberts House preserves memories from 1867 in a beautiful Victorian mansion. Guests can examine a collection of period toys, furnishings, art, and other relics, offering a rare look into the old days.
Also, Cumberland has an active arts community whose works visitors can sample at the Cumberland Theatre. Enthusiasts come to watch high-class musicals, dramas, and comedies in the region's sole professional theatre.
Thurmont
True to its moniker, Thurmont treats tourists to a rare getaway to the mountains, exposing them to the hidden magnificence of the Catoctin Mountains. This fairytale destination promises endless adventures across its rugged wilderness. A visit to Cunningham Falls State Park introduces newcomers to the state's highest waterfall. The 78-foot cascading facade of Cunningham Falls leaves many in awe of the unmissable photo opportunity.
Furthermore, rock climbers, campers, and hikers find the best pursuits at the 5,000-acre Catoctin Mountain Park. The reserve harbors wooded trails with rocky climbs and primitive campsites throughout its rugged expanse. Thurmont also welcomes wildlife enthusiasts to witness exotic species at the Catoctin Wildlife Preserve. The small but intimate sanctuary provides a refuge for meerkats, zebras, and other popular species.
Ocean City
Ocean City is easily one of the most popular small towns in Maryland, offering tourists the perfect mix of cozy weather, stunning beaches, and soothing water views. Set along the Atlantic Coast, beach lovers flock to the small towns to make the most of sunbathing and picnicking along the sandy stretches of Ocean City Beach. The neighboring Ocean City Boardwalk keeps visitors engaged along a lively corridor with craft vendors, small pubs, trendy eateries, and souvenir shops.
Families out to have fun can select from a long list of thrill rides to get their adrenaline pumping at the Jolly Roger Amusement Park. This lovely destination features an impressive mix of roller coasters, water slides, and a giant Ferris wheel overlooking the shiny ocean waters. Alternatively, you can embrace a classic scare with a dark tour of Trimper's Haunted House for unforgettable encounters.
Berlin
Berlin boasts a picturesque historic district lined with rustic Victorian storefronts, framed by beautiful backcountry with exquisite natural treasures. The vibrant town square houses a mix of galleries, museums, and restaurants, with noteworthy venues like the Calvin B. Taylor House providing a glimpse of Berlin in the 1830s. This Federal-style dwelling retains its structural integrity, as well as unique furnishings and artifacts from the period. While exploring the neighborhood, you can try Berlin's lasting craft beer culture at Burley Oak Taproom & Brewing Company.
Beyond the busy downtown, a quieter and more serene scene awaits at the Assateague State Park. This dreamy destination conceals a charming mix of clean beaches, sandy trails, and grassy shores where wild ponies and other native wildlife exist nonchalantly.
Chestertown
Chestertown has a picturesque setting along the Chester River and charms visitors with its unmatched historical heritage, vibrant arts district, and awesome water views. According to the Historical Society of Kent County, the town was established at the start of the 19th century. Its enduring history is deeply chronicled by piles of memorabilia, manuscripts, and archives inside the museum. The Garfield Center for the Arts is the cultural hub in the region and frequently stages a lineup of dramas, comedies, musicals, and other stage presentations to excite the crowds.
Every Saturday, the town welcomes the Chestertown Farmers' Market, which showcases the diversity and vibrancy of its residents. This family-friendly spectacle features an assortment of farm produce, artisanal goods, baked items, and gourmet dishes by various vendors from the locality.
Cambridge
Cambridge is another appealing town on the Eastern Shore set along the banks of the Choptank River. It is known for its enduring history and rejuvenated downtown, where you can find a vibrant mix of museums, galleries, and local businesses. The imposing Choptank River Lighthouse turns heads with its rare screwpile design, a reminder of Cambridge's maritime heritage. However, you can get a clearer idea of the same by visiting the Richardson Maritime Museum, where piles of artifacts highlight almost three centuries of the area's nautical past.
Downtown is home to the Dorchester Center for the Arts, an all-around cultural venue where visitors can attend an art class, admire an exhibition, or watch a stage performance. Just south of the town, the Blackwater National Wildlife Refuge compels visitors to change the scenery and discover a beautiful 30,000-acre sanctuary with ponds, forests, marshes, and hiking trails harboring a thriving native wildlife population.
Havre De Grace
This small town's unmatched beauty is underscored by its setting on the confluence of the Susquehanna River and the Chesapeake Bay. The dramatic scene of the two waterways interacting leaves many in awe, with front-seat views reserved at the Havre de Grace Promenade. From the quiet platform, guests will also notice the towering Friends-Concord Point Lighthouse, which rises over the town. This imposing structure was installed in 1827 and reminds first-timers of its vital role during maritime expeditions on the Chesapeake Bay.
Havre de Grace's downtown is chock-full of historical treasures, starting with the Lock House Museum. This 19th-century structure stores curious archives documenting the history of the Tidewater and Susquehanna canals. Meanwhile, outdoor lovers can explore the riverside Susquehanna State Park, which boasts heavy forest cover with rocky terrain and opportunities for hikers, fishermen, campers, and more.
The Old Line State never fails to amaze visitors in the United States, whether you are touring for the first time or you have been going there for years. This is thanks to the small fairy-tale towns in Maryland that give it its true identity with their diverse combination of unexplored traditions, absorbing histories, and pristine backcountry beauty. Wherever you visit, expect a novel experience that will forever linger in your memory, from the adventurous hikes through the mountains of Thurmont to the majestic sails along the river in Cambridge.
