10 Fairy-Tale Small Towns In Maryland
Maryland is small enough to cross in a morning, yet it hides an outsized collection of storybook towns, the kind with covered bridges over trout streams, gaslit Victorian main streets, stone mills climbing a river gorge, and mountain villages where a steam train still whistles through the fall color. Skip the interstates and the big cities, and the Old Line State turns into something closer to a fable. These ten small towns look like they were drawn for a picture book, and every one of them is real.
Ellicott City
If any Maryland town was built for a fairy tale, it is Ellicott City, a stone mill village tumbling down a steep wooded gorge where the Tiber River meets the Patapsco. Founded in 1772 by three Quaker brothers who turned it into one of the largest milling operations in the colonies, its Main Street is a near-vertical run of 18th- and 19th-century stone buildings, antique shops, and taverns stacked against the hillside.
At the bottom of the hill sits the B&O Ellicott City Station, built in 1830 and the oldest surviving railroad station in the country, now a free museum with the original station bell and a model layout of the first 13 miles of track ever laid in America. Climb to the ruins of the Patapsco Female Institute, an 1830s finishing school turned hilltop overlook, for the view back down over the rooftops.
Cumberland
Wrapped in the folds of the Allegheny Mountains, Cumberland is the gateway to Maryland's storybook west, and its skyline of church spires against the ridgeline looks lifted from a European postcard. The best way to see the color is from the Western Maryland Scenic Railroad, whose restored train winds up the mountains toward Frostburg through some of the most cinematic fall scenery in the mid-Atlantic.
Downtown, the pedestrian mall runs past the 1867 Gordon-Roberts House, a Victorian mansion packed with period toys and furnishings, and the Cumberland Theatre keeps a professional company staging musicals and drama. The town also marks the eastern end of the 150-mile Great Allegheny Passage, so cyclists roll in straight off the mountains.
Frostburg
Higher up the same mountains, Frostburg is the other end of that scenic railway, a college-and-coal town perched at nearly 2,000 feet where the steam train pulls in and turns around on a working turntable. Its compact 19th-century Main Street climbs the hillside in a run of locally owned shops, cafes, and preserved brick storefronts, with the Appalachian ridgelines filling the gaps between buildings.
The 150-mile Great Allegheny Passage rolls right through town, giving hikers and cyclists a flat, tree-lined path toward Pittsburgh in one direction and Cumberland in the other. Between the railway, the trail, and Frostburg State University, the little town stays livelier than its mountain-hamlet looks let on.
Oakland
In Maryland's far western corner, deep in Garrett County's high country, Oakland is a mountain town straight out of a storybook, complete with a picture-perfect 1884 B&O railroad station in the middle of downtown. It makes an ideal base for the wilds of the surrounding plateau, where old-growth hemlocks and rushing water do the enchanting.
Just outside town, Swallow Falls State Park hides Muddy Creek Falls, at 54 feet the tallest free-falling waterfall in the state, along with a trail that threads a canyon beneath a grove of hemlocks some of them centuries old. Nearby Deep Creek Lake, the largest inland lake in Maryland, adds boating and a ring of forested shoreline to the western-mountain escape.
Thurmont
Cradled in the Catoctin Mountains, Thurmont has the most literal fairy-tale credential of any town here: covered bridges. The red Loys Station and Roddy Road spans still carry roads over local creeks, the kind of postcard structures most states have long since paved over. The mountains behind town hide the presidential retreat of Camp David, tucked away in the same woods.
Cunningham Falls State Park draws visitors to Cunningham Falls, a 78-foot cascade that is the state's tallest, while the adjoining Catoctin Mountain Park lays out 5,000 acres of rocky, wooded trails and primitive campsites. For something unexpected, the Catoctin Wildlife Preserve keeps meerkats, zebras, and big cats in the Maryland hills, an odd and delightful wrinkle in a mountain town.
Berlin
Berlin is so postcard-perfect that Hollywood keeps casting it: the Victorian storefronts and brick sidewalks of its historic downtown stood in for small-town America in "Runaway Bride" and "Tuck Everlasting." The result is a main street that genuinely looks like a movie set, anchored by the 1895 Atlantic Hotel and lined with galleries, antique shops, and the well-loved Burley Oak Brewing Company.
The 1830s Calvin B. Taylor House Museum preserves a Federal-style home full of period furnishings, and just outside town the wild ponies of Assateague roam the dunes and beaches of Assateague State Park. Storybook streets and wild horses within a few miles of each other is a hard combination to beat.
Chestertown
On the Eastern Shore, Chestertown lines the Chester River with one of the finest collections of 18th-century brick townhouses in the country, a colonial waterfront so intact it feels frozen mid-century. Founded in 1706, it was once Maryland's second-largest port, and its High Street still runs past Georgian mansions to the water where tall ships tie up.
The Garfield Center for the Arts anchors a lively downtown theater scene, and every Saturday the Chestertown Farmers' Market fills Fountain Park with produce, baked goods, and artisans. Time a visit for the annual Chestertown Tea Party Festival, when the town reenacts its own colonial-era protest with costumes and a river full of period boats.
St. Michaels
St. Michaels is the Chesapeake at its most enchanting, a Victorian harbor town nicknamed "the town that fooled the British" for the legend that residents hung lanterns in the trees during the War of 1812 so cannon fire would sail overhead. Its harbor and gingerbread-trimmed streets make it one of the Eastern Shore's most photographed spots.
The Chesapeake Bay Maritime Museum spreads across an 18-acre waterfront campus crowned by the 1879 Hooper Strait Lighthouse, a screwpile beacon you can climb for harbor views. A Patriot Cruises sail rounds out the visit, gliding past centuries-old captains' mansions along the Miles River.
Havre de Grace
Where the Susquehanna River pours into the head of the Chesapeake Bay, Havre de Grace strings its prettiest sights along a waterfront promenade. At its end stands the Concord Point Lighthouse, built in 1827 and one of the oldest continuously operated lighthouses on the East Coast, a squat white tower straight off a nursery-rhyme page.
The boardwalk connects a string of small museums, including the Havre de Grace Decoy Museum, a shrine to the folk art of Chesapeake duck decoys, and the 19th-century Lock House, last survivor of the Susquehanna and Tidewater Canal. Just upriver, Susquehanna State Park adds forested trails and a working 18th-century grist mill.
Cambridge
Rounding out the Eastern Shore, Cambridge sits on the Choptank River with a High Street of grand Victorian and colonial homes leading down to the water. The red screwpile Choptank River Lighthouse, a faithful reconstruction of the 1871 original, marks the harbor, while the Richardson Maritime Museum keeps nearly three centuries of Chesapeake boatbuilding afloat.
South of town, the Blackwater National Wildlife Refuge unrolls 30,000 acres of marsh, forest, and open water, home to one of the East Coast's densest populations of bald eagles. Drive its Wildlife Drive at dawn and the mist-covered marshes feel about as enchanted as Maryland gets.
The Old Line State's Fairy-Tale Side
From a stone mill town spilling down a river gorge to covered bridges in the Catoctins, a steam train climbing the Alleghenies, and lantern-lit harbors on the Chesapeake, Maryland hides more storybook scenery than a state this size has any right to. Ride the rails out of Cumberland, chase waterfalls near Oakland, or wander Berlin's movie-set streets: whichever you pick, the Old Line State has a fairy tale waiting off the main road.
