6 Cutest Small Towns In Maryland To Visit

Maryland packs a startling amount of personality into towns barely bigger than their main streets. Container ships slide past restaurant decks on a working canal. A lighthouse from the 1820s still opens for climbing on Saturdays. A stone tower honored George Washington nearly 60 years before the capital finished its own. And every one of these towns has a scene of its own.

Chesapeake City

Three short blocks of restored Victorian storefronts climb up from the canal. Fresh paint makes the whole waterfront look scrubbed clean. That little district is the heart of Chesapeake City, a Cecil County town of fewer than 800 people. The town stands at the western mouth of the Chesapeake and Delaware Canal. The canal still works. Finished in 1829, it carries commercial shipping between the Chesapeake Bay and the Delaware River. The town's North Basin opens right onto that traffic. The C&D Canal Museum occupies the original 1837 pump house, run by the Army Corps of Engineers. Inside, a giant waterwheel once pulled water from Back Creek to top up the canal.

The Ben Cardin C&D Canal Recreational Trail covers 16 paved and crushed-stone miles along the south bank. Walkers and cyclists both use it. Bayard House Restaurant on Bohemia Avenue has fed people since 1829, and the building dates to 1780. Its deck hangs right over the canal, crab cakes and all. Schaefer's Canal House stands at the basin entrance. Diners there watch freighters slide past the windows.

Havre de Grace

Trim Victorian streets slope down to the water's edge in Havre de Grace. This Harford County town of about 15,000 lies where the Susquehanna River spills into the head of the Chesapeake Bay. Concord Point Lighthouse marks the spot, built in 1827 and the second-oldest in the state. It opens for climbing on spring-through-fall weekends. The half-mile Promenade boardwalk links it to the city yacht basin past Tydings Memorial Park.

The Havre de Grace Decoy Museum on Giles Street holds one of the country's biggest collections of working waterfowl decoys, a nod to the old Susquehanna Flats market gunners. A few blocks north, the Maritime Museum offers hands-on boatbuilding and a living oyster reef. MacGregor's Restaurant & Tavern works the waterfront for dinner. Tidewater Grille at the marina plates crab with a view straight up the Susquehanna.

Solomons

A boardwalk wraps the little island village of Solomons, in southern Calvert County where the Patuxent River joins the Chesapeake Bay. The Calvert Marine Museum on Solomons Island Road is the headliner. It holds the Drum Point Lighthouse, a hexagonal cottage built in 1883. The museum also has live river otters and a paleontology hall. Its Miocene fossils erode straight out of the nearby cliffs.

Ten miles north, Calvert Cliffs State Park has a 1.8-mile trail down to the beach. People hunt there for shark teeth, 10 to 20 million years old, that the cliffs shed constantly. Three miles west, the Annmarie Sculpture Garden & Arts Center scatters more than 30 sculptures across 30 wooded acres along St. John Creek. Evenings, the Solomons Island boardwalk gets busy around Stoney's Seafood House and the marina's Tiki Bar. That bar has poured drinks every summer since 1974.

Thurmont

Three red covered bridges still carry cars over the creeks around Thurmont, the kind of postcard scene most towns only wish for. This Frederick County town of nearly 7,000 lies at the foot of the Catoctin Mountains. Cunningham Falls State Park begins three miles west. It holds Maryland's tallest cascading waterfall at 78 feet. The 43-acre Hunting Creek Lake has a sandy swim beach, open Memorial Day through Labor Day. The park covers more than 6,000 acres of hardwood and hemlock and links by trail to its federal neighbor.

Catoctin Mountain Park is the National Park Service half of the same ridge. It offers 25 miles of trails and one famous off-limits tenant: Camp David hides inside the boundary. The Catoctin Wildlife Preserve and Zoo on US-15 covers 50 acres of bears, snow leopards, and reticulated giraffes. The three covered bridges date to 1856 (Roddy Road), 1880 (Loys Station), and 1850 (Utica Mills). Utica Mills was hauled over from the Monocacy River after an 1889 flood.

Boonsboro

A tight Main Street of brick and stone storefronts lines the old National Road. A restored 1796 stone inn holds down the square. Boonsboro is a Washington County town of about 3,800 at the foot of South Mountain. Crystal Grottoes Caverns opened to the public in 1922. Its limestone chambers pack in more formations per square foot than just about any cave around. Four miles east, Washington Monument State Park protects a 40-foot stone tower. Townspeople raised it on July 4, 1827, the first completed monument anywhere to George Washington.

The Appalachian Trail threads through that park and nearby Greenbrier State Park. Greenbrier's 42-acre lake comes with its own sand beach. Two AT overlooks north of town, Annapolis Rock and Black Rock Cliff, look west across the valley. The Boonesborough Museum of History on North Main Street is a wonderfully odd private collection. The late Doug Bast spent a lifetime gathering its Civil War, Native American, and Egyptian artifacts.

Cumberland

Brick storefronts and a skyline of church spires make downtown Cumberland look like a city shrunk to fit a mountain valley. The seat of Allegany County lies in the western panhandle, where Wills Creek meets the Potomac River. Its population is around 18,500. Canal Place Heritage Area marks the western end of the Chesapeake and Ohio Canal. The C&O Canal Visitor Center occupies the restored Western Maryland Railway Station. From that depot, the Western Maryland Scenic Railroad makes 32-mile round trips to Frostburg. A restored steam locomotive pulls them Saturdays and Sundays, May through October.

The Washington Street Historic District lines up Federal, Greek Revival, and Victorian buildings along ten blocks. Look for the 1893 Allegany County Courthouse and the 1867 Gordon-Roberts House, now the History House museum. Emmanuel Episcopal Church (1850) stands on the old grounds of Fort Cumberland. A young George Washington served there as a colonel in 1755. The Great Allegheny Passage covers 150 miles north out of Canal Place to Pittsburgh. It ties into the C&O Canal Towpath right here, opening a 335-mile route to Washington, DC.

A Different Kind Of Pretty Each Time

Each town earns its reputation a different way. Million-year-old shark teeth wash up on the sand at Solomons. A steam locomotive climbs into the mountains behind Cumberland's old depot. Decoy carvers work the waterfront at Havre de Grace, and a lit cavern winds under Boonsboro's Main Street. Three covered bridges cross the creeks around Thurmont. Chesapeake City sets its tables along a canal that has worked since 1829. The good looks are about all they share.