2024's 7 Most Beautiful Small Towns in Maryland
Maryland, one of the original 13 colonies in the United States, is known as "America in Miniature" because of the diverse landscapes, ranging from mountains and forests to beaches and urban centers, packed into its 10,460 square miles. The state has a rich history, with Annapolis serving as the nation's first peacetime capital and home to the U.S. Naval Academy. Maryland's role in the War of 1812 defending Baltimore inspired "The Star-Spangled Banner." Maryland's small towns like St. Michaels, St. Mary’s City, Berlin, Havre de Grace, Oakland, and Chestertown, each offer a unique blend of history, scenic beauty, and vibrant local culture, easily earning them a spot as 2024’s seven most beautiful small towns.
St. Michaels
St. Michaels is a picturesque town on the Chesapeake Bay within a few hours' drive of both Washington, D.C. and New Jersey. St. Michaels is known for its rich maritime history, charming downtown, and beautiful natural surroundings. With its impressive nautical history, no visit to St. Michaels is complete without a stop at the Chesapeake Bay Maritime Museum (CBMM), which gives visitors a deep dive into the region’s maritime history. With interactive exhibits, historic boats, and a working shipyard, visitors can explore the CBMM’s 18-acre campus and see the 1879 Hooper Strait Lighthouse.
With its unique location on the Miles River, from the museum, visitors can set sail for a harbor cruise in the Chesapeake Bay, book a fishing charter to fish for striped bass, or enjoy a relaxing day by the water browsing the unique shops along Talbot Street, sipping wine and enjoying famous Maryland blue crab at Foxy’s Harbor Grille. Finally, this maritime town loves its festivals, from its WineFest in April to its October Oysterfest and its annual harvest festival, Fall into St. Michaels, in October 2024; there’s never a wrong time to visit.
Saint Mary’s City
Just over two hours south of Baltimore, this historic small town is one of the oldest colonial settlements in the United States and was the first capital of the state of Maryland. Visitors to Saint Mary’s City may feel as if they have stepped back into the 17th century, as the town is a reconstructed colonial town where they can see colonial buildings and learn about the lives of the early settlers from costumed interpreters. Another way to experience authentic colonial life is touring the Maryland Dove docked in St. Mary’s River on the shore of the Chesapeake Bay. The ship is a replica of a 17th-century trading ship that brought the first European settlers to Maryland in 1634.
Other not-to-be-missed exhibits include the Brick Chapel (ca. 1667), where visitors can view original lead coffin coverings of 17th-century colonists, the reconstructed State House of 1676, and the St. John’s Site Museum on the campus of renowned liberal arts college, St. Mary’s College of Maryland.
Berlin
Berlin is a small town located just ten miles from the iconic resort town of Ocean City in eastern Maryland and a short drive from Assateague Island National Seashore—a pristine barrier island known for its wild horses and beautiful beaches. Like many of Maryland’s charming small towns, history permeates Berlin with its antique shops, galleries, cafés, and restaurants, all housed in historic buildings—of which 47 are listed on the National Register of Historic Places. To learn more about historic Berlin, visit the Calvin B. Taylor House Museum, the one-time home of a prominent banker and businessman.
Known as "America’s Coolest Small Town,” Berlin is known for its vibrant arts scene, historic buildings, and quaint shops. The Berlin Commercial District is a National Register Historic District. It is home to several unique shops like the Greyhound Indie Bookstore and Fine Art Gallery, House—a one-of-a-kind home décor store, the Sterling Tavern, and the Burley Oak Brewing Company. Art lovers will enjoy strolling along the downtown streets, wandering into galleries like the Mermaid Museum or the funky antique+souvenir store Outten’s Delites. For live music, visit the Globe in a historical 100+-year-old theater.
Havre de Grace
Visitors will find the historic town of Havre de Grace, where the Chesapeake Bay meets the Susquehanna River, a 444-mile-long river that runs through Maryland, Pennsylvania, and New York. Discover the town by walking along the promenade, which is a scenic mile-long boardwalk with picturesque views of the river with stops along the way at the Havre de Grace Maritime Museum, the Havre de Grace Decoy Museum which maintains an impressive collection of well-known Chesapeake Bay decoys, and the Concord Point Lighthouse built in 1827 before being decommissioned in 1975, and the nearby Keeper’s House Museum.
For seafood lovers, Havre de Grace has some pretty waterfront restaurants like the Tidewater Grille on the banks of the river or Water Street Seafood. Bomboy’s is a local landmark for a sweet treat, with a delicious selection of homemade ice cream and candy. Contributing to the town’s vibrant cultural scene, the newly-restored Havre de Grace Cultural Center at the Opera House hosts various cultural events, including theater performances, concerts, art exhibits, and film screenings.
Oakland
Oakland is a picturesque town with a mix of natural beauty, historic charm, and quite a few museums for a small town of about 1,800 residents. The Oakland B&O Railroad Museum highlights the importance of the Baltimore and Ohio Railroad, one of the first significant railroads to connect the Eastern Seaboard to the interior of the United States. Another museum devoted to the history of transportation in the region is the Garrett County Transportation Museum, which features vintage cars, trucks, and other vehicles.
Outdoor enthusiasts can explore the 1.25-mile train through Swallow Falls State Park, a stunning park with a picturesque crashing 53-foot waterfall, Muddy Creek Falls. The Youghiogheny River flows along the park's borders, passing through shaded rocky gorges and rippling rapids—some of the most breathtaking scenery in Western Maryland. From October 9 to 13, 2024, Oakland hosts its 57th Annual Autumn Glory Festival, a five-day festival celebrating the beauty of the local fall foliage.
Leonardtown
Leonardtown is a quaint town in St. Mary's County. Visitors can explore the town’s historic district on a self-guided walking tour, discover well-preserved buildings, and learn about the area's history. Initially built in 1744, Tudor Hall was the home of Philip Key, uncle of Francis Scott Key, who wrote “The Star-Spangled Banner.” Legend has it that George Washington once visited Tudor Hall and likely slept there. Another famous landmark in Leonardtown is the Old Jail Museum, built in 1876 and used until 1945 by the oldest sheriff’s office in the nation.
Visitors to Leonardtown can stroll through the charming downtown area, the Leonardtown Arts & Entertainment District, shop for unique items, and dine in cozy, local restaurants like the Olde Town Pub, the Front Porch, or Sweetbay Restaurant & Bar. The Leonardtown Butterfly Trail in the A&E District takes visitors through historic landmarks, outdoor spaces, and hidden works of art marked by butterfly banners and flags created by a local Leonardtown artist.
Chestertown
Founded in 1706, Chestertown has a rich colonial history and is famous for hosting the 1774 Chestertown Tea Party—a protest against British taxation that echoes the spirit of the American Revolution. It is also home to the prestigious Washington College, founded in 1782. The town features a well-preserved historic district with 18th-century architecture, like the 1733 White Swan Tavern, a landmark inn restored to its colonial-era grandeur. It now operates as a bed-and-breakfast but hosts events and has a tea room where visitors can enjoy a quiet, historic setting. Another popular local restaurant in a historical setting is the Kitchen at the Imperial, a restaurant known for its upscale dining experience focusing on seasonal, locally sourced ingredients.
Its location along the scenic Chester River makes this town of about 5,600 residents the perfect spot to host one of the largest annual gatherings of Tall Ships in North America, known as the Sultana Downrigging Festival, from November 1 to 3, 2024. The festival features three days of music, sailing, ship tours, lectures, exhibits, and family activities, celebrating the culture and community of Chestertown and the broader Chesapeake Bay region.
Maryland’s small towns are rich in history, with 19th-century architecture, vibrant arts scenes, and maritime heritage. Visitors can explore charming streets, historic landmarks, and local museums, like those in St. Michaels, Havre de Grace, and Oakland, highlighting the region’s maritime and transportation history. Outdoor enthusiasts will find scenic parks and trails like those around Leonardtown. Local festivals, unique dining, and boutique shopping add to the charm. Each town provides a unique experience, making Maryland’s small towns ideal for history buffs, nature lovers, and culture seekers.
