9 Maryland Towns With Unforgettable Main Streets
Main Street in Annapolis runs five blocks downhill to the Chesapeake Bay, and you can see most of what the town is about before you reach the water. That is the trick of a good Maryland main street: park once and the shops, the museums, the bars, and the people you came to see all sit within a few hundred steps of one another. In Berlin the whole town turns out on the same block on a Friday night. In Cumberland the street is a pedestrian mall with no cars on it at all. You do not plan a day around these places so much as wander into one.
What follows are nine Maryland towns built for that kind of walking. Each one keeps its restaurants, its history, and its waterfront close together, so a single afternoon on foot is enough to get the feel of the place.
Annapolis
Main Street in Annapolis runs five blocks downhill to the City Dock, lined with 18th-century storefronts the whole way down. The walk ends at the water, where boat owners and gawkers gather along the narrow finger of harbor that locals call Ego Alley, named for the slow parade of vessels that motor in just to be seen. Sailors, midshipmen from the Naval Academy, and weekend crowds share the same few blocks of brick.
The history sits right on the walk. The Maryland State House, two blocks up from the dock, is the oldest U.S. state capitol in continuous legislative use, dating to 1772, and the only one that ever served as the nation's capitol. Inside, the restored Old Senate Chamber is where George Washington resigned his commission in 1783. A few blocks down is the William Paca House and Garden, the restored 1760s home of a Declaration of Independence signer who later became Maryland's governor; its two-acre garden is walled off from the street and easy to miss if you do not know to look.
Berlin
Berlin won Budget Travel's "America's Coolest Small Town" title in 2014, and the town that turned out to vote for it still fills Main Street on a Friday evening. The downtown runs a few compact blocks of restored storefronts, and the people are the point: this is a place that holds bathtub races down the street in June and a New Year's ball drop in winter. Movie crews noticed the look too, filming "Runaway Bride" and "Tuck Everlasting" on these blocks.
Right on Main Street, the Calvin B. Taylor House Museum occupies a Federal-style home built in 1832, where volunteers walk you through the town's story from the 1800s on. For the night, The Atlantic Hotel has anchored the same corner since 1895, its Victorian porch lined with rocking chairs that face the street. Next door, Oaked at the Globe puts dinner and live music inside an old theater, and the crab cakes are the thing regulars order.
Easton
Easton's downtown gathers along Washington and Harrison Streets, two blocks of Colonial and Victorian fronts that the Eastern Shore treats as its cultural center. The crowd here moves between the stages and galleries. The 1922 Avalon Theatre, restored and seating 400 under an 18-foot dome, brings in the music and comedy acts, and a five-minute walk away the Academy Art Museum hangs rotating shows in five galleries and charges nothing to get in.
Even the hotel is part of the walk. The Tidewater Inn has stood on the same downtown street since its present building opened in 1949, with a separate 1874 mansion, the Tidewater House, kept nearby. The Trippe Gallery sits on the same block, showing work from more than 40 artists, so a person can see a play, a museum, and a gallery without moving the car.
Cumberland
Cumberland did the thing most downtowns only talk about: it closed Baltimore Street to cars. The pedestrian mall is the spine of downtown, set against the Allegheny Mountains with the Potomac River close by, and people walk it shop to shop with no traffic to dodge. At the foot of it waits the Western Maryland Scenic Railroad, whose steam train runs a 4.5-hour round trip out to Frostburg and back, crossing an iron truss bridge and threading the 914-foot Brush Tunnel along the way. The Polar Express and the murder-mystery dinner runs sell out to repeat riders.
The history is a short walk off the mall. The Allegany Museum fills a 1930s neoclassical building with the story of the region's railroad era, and the Embassy Theatre, a movie house from 1931, still shows films and stages live shows a few doors along. The whole circuit holds together on foot.
Chestertown
Chestertown keeps its life at the corner of High and Cross Streets, where the colonial-era blocks meet at Fountain Park. The park's centerpiece is a cast-iron fountain of Hebe, the Greek goddess of youth, and the same green hosts the Chestertown Farmers Market every Saturday, year-round, where growers and bakers from the surrounding county set up their tables. It is the spot where the town actually runs into itself.
The eating is all within the same few blocks. Evergrain Bread Company bakes its cakes, baguettes, and croissants on site and pours the coffee to go with them. For a fuller plate, Modern Stone Age Kitchen built its name on a nose-to-tail kitchen that uses every edible part of the animal, the kind of menu that gives a small downtown a reputation beyond it.
St. Michaels
Talbot Street is where St. Michaels does its business, a run of Victorian homes turned into galleries and shops in a town that built boats for a living. The water is a block off the street. At the Chesapeake Bay Maritime Museum, 18 acres on the harbor, a working shipyard still turns out wooden hulls and the 1879 Hooper Strait Lighthouse stands open to climb, with the keeper's quarters inside and the Miles River spread out below. Patriot Cruises runs its 65-foot boat eight miles up that river past the old waterfront mansions.
At the south end of Talbot Street, the Lyon Rum Distillery works out of an old flour mill, making its spirits cane to glass. The tasting room pours free samples, and it is an easy last stop before the walk back up the street.
Cambridge
High Street in Cambridge starts among 19th-century fronts downtown and drops straight to the water at Long Wharf Park, the town's gathering place on the Choptank River. People fish off the boardwalk on one side and spread picnics on the grass on the other, and the hexagonal Choptank River Lighthouse sits at the end with a small museum of maritime photographs inside. The walk down High Street is the whole orientation a visitor needs.
Downtown carries Cambridge's heaviest history. The Harriet Tubman Museum and Educational Center, run largely by local volunteers, tells the story of a woman born in this county who returned again and again to lead others out of slavery. A short walk away, RAR Brewing pours sour ales and lagers inside a former pool hall and bowling alley, the sort of reuse that keeps an old downtown occupied.
Brunswick
Brunswick grew up as a railroad and canal town, and Potomac Street still runs beneath multi-story brick fronts with live train tracks alongside. The morning gathering spot is Beans in the Belfry, a coffeehouse set inside a 1910 red-brick church and furnished with mismatched antiques, the kind of room where people linger. A few doors on, Smoketown Brewing pours its beer out of a restored 1948 fire station, trading the coffee crowd for the evening one.
The town's rail past lives at the Brunswick Heritage Museum, where a huge model railroad fills the third floor and the lower two hold the artifacts of the boomtown years, including the canal traffic that ran through before the trains took over. It is a short, level walk from the cafes, which is the whole appeal of the place.
Ocean City
Ocean City does not lean on old brick the way the others do. Its main street is a three-mile wooden boardwalk, and on a summer night the whole town is out on it, moving between the restaurants, bars, and ride lights with the surf on one side. The crowd is the attraction. The Angler Restaurant and Bar sits right on the water and runs sunset cruises off a 65-foot boat for anyone who wants the view from offshore.
The boardwalk's two ends bracket its history. At the south end, the Ocean City Life-Saving Station Museum, built in 1891, keeps the story of the U.S. Life-Saving Service that came before the Coast Guard, with rescue gear and shipwreck relics on display. Across from it, Trimper's Rides has run since 1893, and its 1912 hand-carved Herschell-Spillman carousel still turns, one of the oldest operating carousels in the country.
One Walk, Nine Downtowns
In each one, the people you came to meet and the places worth seeing sit on a single walkable street, whether that street is a colonial hill running down to a harbor, a closed-off pedestrian mall, or three miles of boards along the Atlantic. Annapolis and Cumberland could not look less alike, yet both ask the same thing of a visitor: park once, and walk.
