Maryland's 10 Nostalgic Downtowns That Are Dripping With Americana Vibes

Maryland sits in one of the East Coast's major "golden zones" for tourism. As one of the original 13 Colonies, Maryland has plenty of historical sites and attractions for history lovers to enjoy, with everything from Colonial-era settlements to Civil War battlefields. Maryland's proximity to Washington, DC, also puts it within convenient distance to Washington's many museums and cultural sites. And, with borders stretching from the Atlantic Ocean to the Chesapeake Bay to the Appalachian Mountains, Maryland has extensive outdoor attractions on land and on water. However, the focus on DC-centric communities and outdoor destinations may distract visitors from Maryland's many top-notch cities and towns. This is a shame, because Maryland's many urban centers and small towns have some of the nation's best downtown areas. 

Maryland's downtown communities range from large metropolitan centers to charming small-town Americana. What they all have in common, however, is an emphasis on historic prestige, walkable infrastructure, and modern tourism amenities. As the United States celebrates its 250th anniversary, many Americans can enjoy authentic American nostalgia in one of Maryland's many excellent downtown areas. From big cities to small towns and everywhere in between, these 10 Maryland downtowns offer nostalgic vibes, culturally rich atmospheres, and distinct slices of American history. 

13 miles outside of Baltimore is Maryland's historic and scenic community of Ellicott City. Though less an actual "city" and more an unincorporated community, Ellicott City nonetheless preserves a picturesque historic core dating back to the 1700s. Old Ellicott City retains classic cobblestone streets, historic storefronts, art galleries, and museums, all harkening back to the earliest days of the United States. Ellicott's stop along the Baltimore and Ohio Railroad (America's first major rail route) offers plenty of railroad nostalgia for train lovers, particularly via the Baltimore & Ohio Ellicott City Station Museum, the "oldest railroad station in America."

Moving to coastal Maryland, Havre de Grace is a charming and artsy Chesapeake Bay waterfront destination, with a scenic downtown and bayside vibes. Dating back to 1782, Havre de Grace sits at the intersection of the Chesapeake Bay and the Susquehanna River, so visitors can enjoy historical vibes and natural splendor in one downtown walk. Havre de Grace's riverfront Main Street hosts lovely Victorian homes and boutique shops. History buffs can visit the Concord Point Lighthouse or the Havre de Grace Maritime Museum and Environmental Center to learn about American maritime history.

St. Michaels is a Chesapeake Bay treasure on Maryland's portion of the Delmarva Peninsula. With a history dating all the way back to 1672, St. Michaels arguably preserves more historic heritage than anywhere else in Maryland. The town's waterfront setting fosters plenty of laid-back yacht-town vibes that are sure to delight boating enthusiasts. Likewise, the downtown area's walkable streets feature nostalgic boutique shops, galleries, and maritime museums. Visitors can stroll along the downtown St. Michaels waterfront and take in relaxing views of passing sailboats, or taste American history at The Crab Claw, an authentic Maryland crab shack.

Ocean City is a well-known beach vacation spot, but its downtown area offers a more authentic, walkable atmosphere than just upscale beachside resorts. Downtown Ocean City includes much of its famous oceanside boardwalk, complete with beach food stands, arcade games, and beautiful views of the Atlantic. While not as historic as Maryland's Colonial-era towns, Ocean City's downtown does date back to the early 20th century. A walk here will conjure all of the classic vibes of America's summer beach getaways from pop culture. Visitors can explore historic hotels, maritime museums, and nostalgic amusement park attractions. 

Hagerstown is Maryland's "Gateway to the West," linking the mountainous western Maryland with the rest of the state. The city is rich in outdoor attractions and historic sites, but Downtown Hagerstown has a memorable blend of old charm and modern experiences. Main Street Hagerstown is part of the Main Street Maryland historic preservation program, with a vibrant cultural trail filled with public art, several museums, and excellent outdoor dining options.  Beyond the many individual businesses, Downtown Hagerstown's districts are filled with colorful buildings displaying different architectural styles.

Maryland's Eastern Shore community of Berlin is a distinctly American small town, name notwithstanding. Smithsonian magazine even named Berlin as one of the "best small towns to visit in 2016," and its thriving downtown area will quickly tell you why that's still true today. Berlin's Main Street features red brick buildings that harken back to the late 18th century. Much of the area's prestige stems from the Berlin Commercial Historic District, which incorporates 18th-century stables and coach stops into a walkable living museum. Here, the town's dozens of registered historic landmarks mingle with a modern arts and shopping district. 

Located 45 miles northwest of Washington, Frederick is a bit removed from the D.C.–Baltimore urban corridor. This may end up being to the city's benefit, however, as visitors can enjoy Frederick's historic streets and gorgeous views without getting distracted by the draw of larger cities nearby. Downtown Frederick is ground zero for central Maryland's blend of traditional vibes, historic buildings, and modern experiences. Visitors can stop at more than 250 charming boutique shops, art galleries, and fine dining restaurants, all while taking in views of a 50-block district that's earned the title of a "Great American Main Street."

Among cities, Cumberland may have Maryland's most unique geography. Planted in the narrow corridor between Pennsylvania, West Virginia, and Western Maryland, Cumberland is a scenic, artistic, and recreational city hidden in Maryland's mountains — with a historic downtown to match. This destination features beautiful 18th- and 19th-century buildings framed against the rolling Appalachian Mountains. Cumberland's Main Street has modern outdoor shopping areas surrounded by century-old city streets, churches, and urban architecture. Downtown visitors can also walk to nostalgic historical attractions like the Western Maryland Scenic Railroad and the C&O Canal Towpath. 

You may know Annapolis as Maryland's capital city, or the home of the United States Naval Academy. However, Annapolis is also a beautiful city all its own, with an enchanting downtown and alluring views of the Chesapeake. Downtown Annapolis is particularly attractive for sailing enthusiasts, with marinas upholding the city's proud maritime heritage. On land, Downtown Annapolis contains traditional brick sidewalks and some of the country's best-preserved 17th- and 18th-century houses, including historic homes of four signers of the Declaration of Independence. Annapolis' Maryland Avenue is also a top-tier downtown stop for shopping, dining, and cultural experiences. 

Being Maryland's largest city, Baltimore would seem like the obvious choice for the state's best downtown area. Baltimore's reputation as a tougher, post-industrial city, however, often obscures its many amazing downtown attractions, artistic scene, and historic vibes. Downtown Baltimore's famed Inner Harbor offers outstanding urban walks with views of both the Chesapeake and the Baltimore skyline. This city also has additional downtown neighborhoods with unique attractions, vibes, and nostalgic character. You can explore one of America's coolest streets along Baltimore's artistic 36th Street (AKA "the Avenue"), or relive American History at Baltimore's Fort McHenry National Monument (of Star-Spangled Banner fame).