10 Historic Maryland Towns Ideal For A Weekend Drive
Maryland’s scenic roads wind through towns that feel like stepping back in time, each corner brimming with history and charm.
Cobblestone streets, waterfront vistas, and local shops invite exploration, while maritime tales whisper from every brick and beam.
These ten destinations promise weekend escapes that trade the city’s noise for a slower, story-filled pace.
1. St. Michaels: Maritime Marvel on the Miles River
Sailboats bob gently in the harbor of this 300-year-old watermen’s village, where the Chesapeake Bay Maritime Museum tells tales of oyster dredgers and skipjacks.
Local lore claims the town fooled British bombardiers during the War of 1812 by hanging lanterns in treetops, earning its nickname “the town that fooled the British.”
Wander along Talbot Street for boutique shopping or savor fresh seafood with harbor views at waterfront restaurants.
2. Chestertown: Colonial Elegance on the Chester River
Red-brick sidewalks lead past Georgian mansions and Federal-style homes in this Eastern Shore jewel founded in 1706.
The town hosts a tea party reenactment each May, commemorating when locals dumped British tea into the Chester River, echoing Boston’s famous protest.
Washington College, the tenth oldest in America, adds youthful energy to this otherwise tranquil riverside community.
Antique hunters find paradise in the many specialty shops dotting High Street.
3. Berlin: America’s Coolest Small Town
Victorian lampposts illuminate brick-paved streets in this former peach-shipping hub that Budget Travel crowned “America’s Coolest Small Town” in 2014.
I stumbled upon Berlin during a wrong turn years ago and found myself lingering for hours, captivated by its 47 historic structures and small-town charm. The locals treat visitors like long-lost friends rather than tourists.
Movie buffs might recognize scenes from “Runaway Bride” and “Tuck Everlasting,” both filmed in this picturesque setting.
4. Oxford: Serene Sanctuary Since 1683
Time slows in Oxford, where the Oxford-Bellevue Ferry, America’s oldest privately operated ferry service, has connected travelers across the Tred Avon River since 1683.
White picket fences frame weathered homes where sea captains once resided, their widow’s walks still scanning the horizon.
The town’s peaceful harbor, dotted with sailboats and working watermen’s vessels, offers the perfect backdrop for sunset strolls along tree-lined streets that have changed little in centuries.
5. Chesapeake City: Canal Town Charm
Perched on the banks of the C&D Canal, this vibrant village offers front-row seats to massive ocean-going vessels passing through the busy waterway.
Candy-colored Victorian homes cluster around the waterfront, many now housing bed-and-breakfasts with porch swings perfect for ship-watching.
I once spent an entire afternoon counting cargo ships from a dockside restaurant, completely losing track of time.
The canal museum explains how this engineering marvel connects the Chesapeake Bay to the Delaware River.
6. Annapolis: Colonial Capital by the Bay
Brick-paved streets spiral outward from Maryland’s capital, where the dome of the nation’s oldest working state capitol building has witnessed history since 1772.
Sailors and midshipmen from the U.S. Naval Academy add a crisp, uniformed presence to the colonial atmosphere of this maritime hub.
Market House anchors the city dock area, where watermen have sold their catches since colonial times and modern pleasure boats now fill what locals affectionately call “Ego Alley.”
7. Ellicott City: Granite Gem in a River Valley
Stone buildings cling to steep hillsides in this former mill town where trains once rumbled through the heart of Main Street.
The Ellicott brothers established their flour mills here in 1772, harnessing the Patapsco River’s power to create one of Maryland’s first industrial centers.
The town has survived devastating floods throughout its history, rebuilding with remarkable resilience each time.
Treasure hunters browse quirky shops housed in granite buildings where mill workers once lived.
8. Frederick: Civil War Crossroads
Church spires punctuate the skyline of Maryland’s second-largest city, where 300 years of architecture create a living museum spanning Colonial, Federal, and Victorian styles.
During my last visit, a local historian pointed out bullet holes still visible in some downtown buildings – silent witnesses to Civil War skirmishes.
Carroll Creek Linear Park flows through downtown, its pedestrian bridges and water features creating perfect picnic spots amid the historic surroundings of this crossroads town that both Union and Confederate armies marched through.
9. Havre de Grace: Where the Susquehanna Meets the Bay
Lighthouse beams still sweep across the water where the mighty Susquehanna River empties into the Chesapeake Bay. Named by Marquis de Lafayette for its resemblance to the French port Le Havre, this waterfront town nearly became the nation’s capital instead of Washington, DC.
The Promenade boardwalk offers stunning water views and glimpses of Concord Point Lighthouse, Maryland’s second-oldest lighthouse.
Decoy carvers continue centuries-old traditions, celebrating the town’s waterfowl heritage at the Decoy Museum.
10. Sharpsburg: Hallowed Ground of American History
Rolling farmland surrounds this tiny town, forever linked to America’s bloodiest single day, the Battle of Antietam.
The clock in Sharpsburg seems frozen at September 17, 1862, when 23,000 soldiers fell during twelve hours of combat that changed the course of the Civil War.
Many original structures that witnessed the battle still stand, including the iconic Dunker Church.
Beyond battlefield history, the town offers scenic views of the Potomac River and access to the historic C&O Canal towpath.