12 Gorgeous Maryland Towns To Visit
Maryland is showing off again. Down on the water, oyster boats glow pink at sunrise and white steeples lean over the harbor. Up in the mountains, a waterfall drops fifty-three feet through the hemlocks. In between, brick rowhouses have faced the river for three centuries. The small towns get all the good views. And they are not subtle about it.
Saint Michaels
St. Michaels curls around its harbor on the Miles River. On a still morning the white steeples and clapboard storefronts double in the water below them. The Chesapeake Bay Maritime Museum takes up the whole point, screwpile lighthouse and all, with a yard packed full of old wooden Bay boats. Talbot Street climbs the hill behind it. The shopfronts only get brighter as you go up.
Past the harbor mouth, the Miles River opens up wide. The best seat in the house is the deck of the schooner Selina II on a sunset sail. When the water goes calm in the evening, the kayakers come out.
Takoma Park
Takoma Park climbs a bunch of shady hills, every house a turreted Queen Anne painted a different color. Locals call it Azalea City. Come spring, the yards go off like fireworks. Old Takoma has the prettiest blocks. The Sunday market spills out behind the Laurel Avenue shops every week.
Sligo Creek threads its green valley right through the middle, under a canopy of old hardwoods. On weekends they close the parkway to cars. The whole leafy stretch belongs to walkers and cyclists.
Havre De Grace
Havre de Grace gets the best light on the upper Bay, right where the Susquehanna pours into the Chesapeake. The Concord Point Lighthouse has stood guard over that spot since 1827, white and trim above the promenade. Walk the boardwalk and you pass the Decoy Museum, full of hand-painted wooden birds.
North of town, the vines at Mount Felix Vineyard tumble toward the water below the tasting-room windows. The Vandiver Inn holds down a downtown corner, a turreted Victorian all dressed up for weddings.
Chestertown
Chestertown lines the Chester River with brick Georgian homes that have faced the water for three hundred years. Only Annapolis has more colonial houses in the state. High Street drops straight down to the waterfront through a corridor of restored brick. Fountain Park spreads across the middle of it all under big shade trees.
The tall ship Sultana ties up along the bank, her masts poking above the rooftops. Washington College fills the edge of downtown with white-columned brick from 1782.
Oxford
Oxford is a tree-lined little village almost surrounded by water. It has barely changed since its colonial-port days. White picket fences and 18th-century homes line the Strand along the Tred Avon. The Robert Morris Inn holds the waterfront corner, part of it dating to a colonial home.
The Oxford-Bellevue Ferry has crossed the Tred Avon since 1683. Ride it over and back for the prettiest ten minutes on the Eastern Shore, the village low and green at the water's edge.
Ocean City
Ocean City throws ten miles of bright sand against the Atlantic. The boardwalk lines the south end in weathered planks. Get there at sunrise, before the crowds. That is the best version of the place. Folks have been coming since the first cottage opened back in 1869.
Over on the bay side, the marshes and back channels go orange at sunset behind the high-rises. Stand on the inlet jetty and you take in the whole skyline and the open ocean at once.
Tilghman Island
Tilghman Island narrows down to a working waterfront, home to the last skipjacks in the country that still dredge oysters under sail. Crab boats crowd Dogwood Harbor against a low marsh horizon. You are never more than a few blocks from the water out here.
Down at the southern tip, the Black Walnut Point Inn looks out from a white farmhouse on garden grounds between the bay and the Choptank. Sunsets drop into open water on three sides.
Crisfield
Crisfield reaches way out into Tangier Sound at the bottom of the Eastern Shore, flat and bright and ringed by marsh. Workboats pack Somers Cove Marina, one of the biggest on the lower Chesapeake Bay. The waterfront museum looks out over the same water the watermen work every day.
The ferry to Smith Island leaves from the city dock, an hour out across open Sound. The crossing alone is the pretty part, all low islands and big sky.
Saint Mary's City
St. Mary's City spreads across green bluffs above the river, where the colony's first capital once stood. The reconstructed 1676 State House looks out over a broad lawn down to the water. Costumed interpreters work a colonial farm under open sky.
The Maryland Dove rides at her dock on the St. Mary's River, masts and rigging dark against the trees. St. Mary's College fills one of the prettiest waterfront campuses in the state, right next door.
Leonardtown
Leonardtown gathers around a green square set up above Breton Bay. Restored brick storefronts ring it on every side. The Port of Leonardtown Winery pours from a made-over building right at the edge of downtown.
The Leonardtown Wharf opens onto Breton Bay at the foot of the main street, all boardwalk and marsh grass. Drive a few minutes south and St. Clement's Island stands out alone in the Potomac under a tall white cross.
Boonsboro
Boonsboro lines up along Main Street at the foot of South Mountain. That green ridge fills the view at the end of every block. Stone and brick storefronts line the old National Road through the center of town. The whole backdrop turns gold by late afternoon.
Four miles up the ridge, the original Washington Monument rises in rough fieldstone, the first one ever built for George Washington back in 1827. The Appalachian Trail crosses right past it, with the whole Cumberland Valley laid out below.
Oakland
Oakland holds down Maryland's mountain corner, where the restored 1884 B&O station still stands smack in the center of town. Family-run shopfronts line a tidy main street under that big Garrett County sky.
A few miles out, Swallow Falls State Park sends Muddy Creek Falls fifty-three feet down through old-growth hemlock, the tallest drop in the state. The Youghiogheny pushes past mossy boulders nearby, cold and clear.
Pretty In Every Direction
The Concord Point Lighthouse still throws white light across the head of the Bay at dusk. Skipjacks still lean into the wind off Tilghman. The steeples of St. Michaels still float above the harbor. Up on South Mountain, a fieldstone tower watches the Cumberland Valley turn gold. These are the views Marylanders grew up with and never quite got over. Pick a harbor, a Main Street, or a mountain ridge. The hard part is deciding which one is prettiest.
