8 Picture-Perfect Main Streets In Maryland

Maryland packs a lot of geography into a small state. Cumberland sits under mountain ridges in the west. Ocean City runs a boardwalk along a barrier island. Annapolis has a working harbor. Emmitsburg looks out at the Catoctins. Eight main streets across the state each carry the story of what built the town and what still walks its sidewalks today.

Berlin

Berlin sits about eight miles inland from Ocean City on Maryland's Eastern Shore, close enough to the beach traffic but not on it. Main Street runs brick-lined between the Atlantic Hotel and the Calvin B. Taylor House Museum, a five-minute walk end to end. Budget Travel named Berlin the country's coolest small town in 2014, and the town has traded on that title carefully, adding independent shops and restaurants at a rate that has not overrun the 19th-century commercial buildings.

The Atlantic Hotel is a three-story brick building with a cast-iron cornice and a long front porch lined with rocking chairs. The Taylor House, one door down, keeps its Federal-style face and a garden gazebo out front where the town runs summer concerts. The Sterling Tavern, on the same block, works crab cakes and a dozen rotating drafts, and books up early on Saturday nights.

Sykesville

Sykesville drops into a river valley in Carroll County where the Patapsco meets the old railway line. The town won a Great American Main Street Award in 2011 and has kept the streetscape working since, with independent tenants filling most of the storefronts. Patapsco Distilling Company pours craft spirits out of one of the oldest surviving buildings on the block. Gypsy Sisters across the street sells hand-sculpted glass, artisan soaps, and spiritual-healing goods, and the window is always worth a second look.

A block over, the Historic Sykesville Colored Schoolhouse is a restored 1904 one-room school that ran as the local segregated classroom for Black students until 1938. The current interpretive space covers early African American education in the county with lesson plans, photographs, and personal accounts from former students and their families.

Cumberland

Cumberland runs a downtown that looks up. The Allegheny ridges rise on all sides, and every intersection on Baltimore Street ends in mountain. The street itself is a pedestrian mall of restored Victorian storefronts, and the Embassy Theatre, a 1931 Art Deco movie house, still runs classic films and live performances a few evenings a week.

The Great Allegheny Passage starts here at Mile 0, with the trailhead marker at the confluence of Wills Creek and the Potomac River anchoring a 150-mile rail-trail that crosses the Eastern Continental Divide on its way to Pittsburgh. Cafe Mark serves breakfast under high ceilings in a brick storefront near the trailhead, useful for either fueling up before the ride or refueling after. The Western Maryland Scenic Railroad runs steam excursions from Canal Place up to Frostburg and back, sharing much of its route with the Great Allegheny Passage through the Cumberland Narrows.

Chestertown

Chestertown is a colonial-era port on the Chester River, on the Eastern Shore across from Annapolis. High Street holds a run of Federal-era mansions built by 18th-century sea captains and merchants back when the town was one of the busiest ports on the Chesapeake. Washington College, founded in 1782, sits at the top of the street.

Fountain Park anchors the middle of town with a cast-iron fountain under shade trees and, every Saturday morning, a farmers' market that draws vendors from three counties. The Garfield Center for the Arts, in a 1920s theater with a lit marquee, runs a full calendar of live theater and hosts an annual ten-minute play festival. The White Swan Tavern down the block, a colonial-era bed and breakfast with six guest rooms, has been putting travelers to bed since Federal times.

Ocean City

Ocean City runs a ten-mile barrier island, and its main street is a boardwalk. The wooden walk stretches from the inlet up to about 27th Street with a steady wall of arcades, funnel cakes, saltwater taffy, and rentable bikes running along the sand side. Trimper's Rides at the south end has been running since 1893 and still turns a carousel of hand-carved wooden animals from that same century.

The Ocean City Life-Saving Station Museum at the Inlet occupies the town's first U.S. Life-Saving Service building, moved and restored, with a small saltwater aquarium and a collection of hurricane artifacts including debris from the storm of 1933 that opened the Ocean City inlet. A cast-iron anchor sits outside the museum for photographs. Farther up the boardwalk, Jolly Roger at the Pier runs the Looping Star coaster and a Giant Wheel that anchors the skyline at the end of the Boardwalk.

Brunswick

Brunswick was a railroad town before it was much else, and the tracks still carry freight and MARC commuter trains through the middle of the street grid. The Brunswick Heritage Museum on Potomac Street runs three floors, and the top floor holds a 1,700-square-foot HO-scale model railroad that recreates the B&O line between Brunswick and Washington Union Station in careful detail, including the actual tunnels and grade crossings.

Beans in the Belfry is a coffeehouse in a converted Gothic-stone church a block off the main drag, with the stained-glass windows still in place and the old pews still in service as booths. Smoketown Brewing next door has taken over a former fire station and pours local beers under the original garage door. Both are the sort of adaptive-reuse projects that look better in person than they sound in a listing.

Annapolis

Annapolis runs its Main Street straight down to the water at Ego Alley, the narrow harbor slot where boat owners parade in and out to be watched. The state capitol, the U.S. Naval Academy, and one of the largest concentrations of 18th-century brick buildings in the country are all within a half-mile walk of the dock. The nickname "Sailing Capital of America" is a claim the town has earned across decades of yacht clubs, boat shows, and racing schools.

The Museum of Historic Annapolis on Main Street covers four centuries of city history over three floors with a mix of period artifacts and interactive displays. Chick and Ruth's Delly on the same block has been running since 1965 and still leads the Pledge of Allegiance every morning at 8:30 sharp. The place is stuffed with political memorabilia and locals who have been coming since childhood, and the crab cakes are better than they need to be.

Emmitsburg

Emmitsburg sits at the northern edge of Frederick County against the Catoctin foothills, with farmland stretching to the south and mountains stacked to the west. Main Street runs Federal-style red-brick homes and vintage cast-iron street lamps, and the ridgeline shows up in nearly every downtown photograph. The Spirit of the American Doughboy stands on the front lawn of the Emmit House, one of the E.M. Viquesney bronze World War I infantry statues that were cast for towns across the country in the 1920s.

Carriage House Inn a block south serves American food in a mid-1800s stone building with a fireplace and a piano bar most evenings. The National Shrine of Saint Elizabeth Ann Seton sits a couple of miles out of town and honors the first native-born American saint. The basilica holds her remains under stained glass, and the gardens outside carry the same quiet the whole ridge line does.

What Maryland Main Streets Have In Common

Maryland's downtowns split into three families. Berlin, Chestertown, and Sykesville run brick storefronts under old-town preservation. Cumberland, Brunswick, and Emmitsburg carry the imprint of the railroad, the ridge, and the mountain in every direction. Ocean City and Annapolis run their main streets down to the water and let the harbor or the boardwalk finish the job. What the eight share is a habit of putting a specific piece of the state's history right at eye level on the sidewalk.