The 10 Most Beautiful Cities in Maryland
Annapolis, situated on the Chesapeake Bay about 30 miles east of Washington, D.C., charms visitors with its maritime heritage and colonial architecture. Strolling through the historic district, you can admire the well-preserved red brick buildings and quaint cobblestone streets, culminating at the Maryland State House, the nation’s oldest state capitol still in continuous legislative use. Kayaking along Spa Creek offers a serene perspective of the waterfront mansions and bustling yacht basins. The best time to visit Annapolis is during the fall when the weather is crisp and the city hosts its vibrant boat shows and seafood festivals, showcasing the bounty of Maryland’s waters.
Heading about 15 miles south of Baltimore, Ellicott City presents a striking blend of history and natural beauty. Nestled in the Patapsco Valley, its Main Street is lined with antique shops, cafes, and art galleries housed in 18th-century buildings. For outdoor enthusiasts, Patapsco Valley State Park offers over 200 miles of trails, with the Avalon Area providing scenic river views and opportunities for fishing and hiking. The 5.8-mile loop through the Cascade Falls Trail highlights a 25-foot waterfall, a refreshing sight after a rain. Springtime blooms and lush summer greenery make this park a year-round escape from the nearby urban bustle.
Oxford, a quaint town on Maryland’s Eastern Shore, lies about 40 miles southeast of Annapolis and is accessible by ferry from nearby towns. Known for its waterfront charm and historic inns, Oxford also boasts the Oxford-Bellevue Ferry, one of the oldest privately operated ferry services in the country. Exploring the town’s wharves and marinas, you can indulge in fresh seafood and watch sailboats drift by. The nearby Tred Avon River invites kayaking and paddleboarding, especially serene during early morning mist or golden sunset hours, when the water reflects a kaleidoscope of colors.
Moving westward, Cumberland rests in the scenic Appalachian foothills, approximately 120 miles northwest of Baltimore. This former industrial hub features the C&O Canal National Historical Park, where the towpath trail stretches 184.5 miles but offers manageable day hikes around Cumberland itself. Walking or biking a few miles along the flat towpath, you can absorb the serene river views and historic canal locks. Autumn is a particularly beautiful season here, as the valley and ridge lines blaze with vivid reds and oranges, ideal for photographers and nature lovers alike.
On Maryland’s scenic western edge, Frostburg sits about 10 miles west of Cumberland and provides access to the Allegheny Highlands Trail. This rail-trail conversion runs 20 miles over gentle grades through forested valleys and open farmland, perfect for casual hiking or cycling. Frostburg itself has a cozy college-town vibe with colorful Victorian homes and a lively arts scene. The annual Frostburg First Friday event showcases local artisans and musicians, best enjoyed during the warmer months when street vendors set up under clear skies.
In the heart of the Chesapeake Bay region lies St. Michaels, a picturesque town on Maryland’s Eastern Shore, roughly 60 miles southeast of Annapolis. Its historic waterfront district is filled with charming boutiques, seafood eateries, and the Chesapeake Bay Maritime Museum. This museum offers extensive exhibits on the bay’s sailing traditions, including restored skipjacks and interactive displays on oyster harvesting. A boat tour from the museum lets visitors experience the bay’s unique ecology firsthand. Spring and early summer are ideal for wildflower blooms and calmer waters, perfect for cruising or exploring the harbor.
Towson, just a 15-minute drive north of Baltimore, combines suburban comfort with cultural richness. The Towson Town Center and the nearby Loch Raven Reservoir offer diverse activities, but the standout is the Hampton National Historic Site. This sprawling 18th-century estate features elegant Georgian architecture and sprawling gardens that vividly illustrate Maryland’s plantation era. The grounds are especially stunning in the fall when the foliage transforms the landscape into a tapestry of warm hues, inviting leisurely walks and historic reflection.
Chestertown, about 70 miles east of Baltimore on the Eastern Shore, exudes colonial charm along the Chester River. The town’s Historic District is a treasure trove of 18th-century homes and public buildings, many open for guided tours. Chestertown also hosts the annual Chestertown Tea Party Festival, a lively reenactment of the town’s revolutionary spirit. Nature lovers can enjoy the nearby Eastern Neck National Wildlife Refuge, a sanctuary for migratory birds and waterfowl. Early mornings in spring or fall bring spectacular birdwatching opportunities against the backdrop of serene marshes and tidal waters.
Ocean City, situated on Maryland’s Atlantic coast about three hours east of Washington, D.C., is famed for its vibrant boardwalk and beachfront charm. The Ocean City Boardwalk stretches over two miles, lined with shops, arcades, and eateries serving Maryland’s iconic crab cakes. For a quieter nature experience, Assateague Island National Seashore lies just south, where wild horses roam free along sandy dunes and salt marshes. Visiting early in the morning or late afternoon offers cooler temperatures and the chance to watch spectacular sunrises or sunsets over the Atlantic Ocean.
Finally, Elkridge, located roughly 10 miles southwest of Baltimore, offers a unique blend of history and nature near the convergence of the Patapsco and Jones Falls rivers. The Patapsco Valley State Park’s Rockburn Branch is a favorite among hikers and mountain bikers, featuring rugged terrain and scenic overlooks. The park’s cascading waterfalls and dense hardwood forests provide a lush escape from urban life. Springtime brings wildflowers and rushing streams, while autumn’s colorful foliage enhances the dramatic landscape, making it a year-round destination for outdoor enthusiasts.