10 Most Beautiful Small Towns In Maryland You Should Visit
Maryland is dotted with beautiful small towns across a mix of mountains to the west and the Atlantic Coast to the east. Dividing its center is the largest estuary in the country, the Chesapeake Bay, where rivers converge with the sea. Numerous historic sites and museums showcase the state’s maritime and railroad lineage. Whether by schooner, train, skis, lighthouse, or bike, there are many ways to experience the scenery and architecture that make Maryland so aesthetically pleasing. From Berlin’s historic inns to the waterfront of Chesapeake City, you should visit these towns for a fun vacation.
Berlin
Berlin is located in Worcester County, Maryland’s easternmost county. The town is known for its tree-lined streets, Victorian town center, and historic homes. Forty-seven individual structures are listed on the National Register of Historic Places, representing nearly two centuries of architectural history. The Berlin Welcome Center is situated downtown and is open 24/7, offering brochures and information on local restaurants, businesses, and attractions. The town center features mostly brick structures, while magnolias, sycamores, poplars, cypress, and ginkgo trees line the streets. Main Street was constructed over a path once taken by Assateague and Pocomoke Indians.
The story goes that Berlin got its name from a contraction of “Burleigh” and “Inn.” The Inn Berlin is a Victorian estate situated on the town’s highest knoll, offering organic linens, a complimentary breakfast, and modern amenities. Its history dates to 1790. It has been largely renovated, yet much of the original interior has been preserved. Pitt’s Street Treasures is another preserver of history. It is an antique mall with more than 65 locally owned booths featuring vintage toys, jewelry, furniture, and other collectibles, most of which are one-of-a-kind.
Leonardtown
Leonardtown is a small community located in St. Mary’s County, Southern Maryland. It is known for its waterways, landscapes, and historic buildings. Downtown is undergoing a renaissance with the addition of specialty shops, galleries, and restaurants. As the only Arts & Entertainment District in the region, Leonardtown offers art classes from artists such as Eric Clark Jackson at Bay Fibers Studio. Jackson created the butterfly banners and flags found around town, forming what is known as the Butterfly Trail. The trail highlights landmarks, outdoor spaces, and hidden works of art.
A butterfly map is available on Leonardtown’s website, while physical copies are available at the Leonardtown Welcome Center at the Old Jail Museum. Built in 1876, the Old Jail Museum was in use until 1945 by the nation's oldest sheriff’s office. Made of granite and brick, it still retains its original upstairs cells and features a store. For more shopping in a historic venue, Shepherd’s Old Field Market contains specialty shops, a burger joint, a beer garden, and an axe-throwing venue.
St. Michaels
Located along the Miles River on the Eastern Shore of the Chesapeake Bay, St. Michaels is known for its maritime history dating back to the 1600s, as a trading post for tobacco farmers and trappers. Its earliest industry was shipbuilding, famous for producing Baltimore clippers, fast schooners capable of evading blockades and outrunning pirates. To learn more, the Chesapeake Bay Maritime Museum explores, preserves, and celebrates the history, environment, and culture of the entire Chesapeake Bay region. The museum offers Patriot Cruises aboard a vessel reminiscent of a 1930s steamboat. The 70-minute cruise includes narration of historic mansions and wildlife along the Miles River.
For accommodation directly on the harbor, St. Michaels Harbour Inn, Marina & Spa is accessible by land or water year-round. It offers boat slip rentals, authentic Eastern Shore cuisine, as well as massages, facials, and body treatments. The rooms feature some of the best views of the water, as does Muskrat Park, home to historic cannons.
Frostburg
Despite its origins as an Appalachian mining town, Frostburg has grown into a mountainous tourist destination. Dans Mountain State Park is located just outside town, perched on a 16-mile-long mountain. It features an Olympic-size swimming pool, pavilions, playground, and pond for fishing. Dan’s Rock Overlook offers sweeping views of the land from 2,898 feet. The Switchback Trail and Sculpture Garden connect the Great Allegheny Passage (GAP) to downtown Frostburg. The sculptures symbolize the consciousness of bicyclists and reflect the creative placemaking found throughout Frostburg.
Also connected to the GAP is the Evergreen Heritage Center, a private family mansion built in the 1780s, now converted into a museum and farm. It is listed on the National Register of Historic Places and offers guided tours. In downtown Frostburg, the Palace Theatre presents a mix of classic, independent, and foreign films in a venue with over 100 years of history.
Thurmont
Thurmont is known as the “Gateway to the Mountains,” as the Catoctin Mountains serve as a backdrop to this northern town in Frederick County. There are several hiking trails to explore within the scenery, many located within Catoctin Mountain Park. Whether beginner or experienced, there are 25 miles of trails to hike. Camping and picnicking are also available. Another trail option is the Thurmont Trolley Trail, built on an old trolley line that served the town in the 1900s. It now begins at an old freight car and powerhouse, featuring murals that memorialize the town’s history.
For cyclists, Thurmont is home to three covered bridges in Maryland. The tour to see all three is around 20 miles with a mix of flat terrain and rolling hills. The oldest covered bridge is 101 feet long, crossing Fishing Creek. It was washed away during a storm in 1889, but was reconstructed by locals. At the base of the Catoctin Mountains, Catoctin Breeze Vineyard produces handcrafted wines.
Havre de Grace
Havre de Grace is located at the head of the Chesapeake Bay where it meets the Susquehanna River. Since 1827, the Concord Point Lighthouse has guided travelers, making it the oldest lighthouse in Maryland still publicly accessible. It is a frequent backdrop for weddings. Concord Point is also home to the Keeper’s House Museum, shining its light on the lives of 19th-century lighthouse keepers. The museum itself is housed in the restored keeper’s dwelling from 1884. The lighthouse park sits within a designated historic district and river promenade, allowing visitors to explore the area.
Also located on the waterfront is MacGregor’s Restaurant, which has served fish-focused fare for more than 35 years, including stuffed rockfish, flounder Milanese, and many crab dishes highlighting the state crustacean, the Maryland blue crab. More than a third of the country’s blue crabs come from the Chesapeake Bay. To get out on the water, BaySail on the Chesapeake offers American Sailing Association courses. It also features a fleet of 22-foot keelboats available for charter, as well as pontoons for rent and sunset cruises.
Chestertown
Chestertown was founded in 1706 on the Chester River, quickly becoming a hub of commerce for tobacco, grain, and other goods important to the growing colonies. In 1774, it hosted the Chestertown Tea Party as an act of protest against British taxation, further contributing to the spirit of the American Revolution. Today, its historic district showcases 18th-century architecture along brick sidewalks. The Kent County Visitor’s Center has maps and brochures available. The Historical Society of Kent County offers a self-guided walking tour and regularly hosts events such as Historic Ghost Walks.
Aiming to restore and preserve the Chesapeake Bay, the Sultana Education Foundation offers programs for adults, families, and classrooms. These include sails aboard the 1768 schooner SULTANA, “Toddler Time,” and more, depending on the season. As a hub of outdoor recreation, Wilmer Park is located on the Chester River and features Aunt Sarah’s Playground, chess tables, and a kayak launch site.
Grantsville
Grantsville’s climate makes it a suitable destination for outdoor recreation during any season. The nearby Wisp Resort offers both downhill skiing and snowboarding in the winter. In the summer, it offers golf courses, aerial and mountain adventures, escape games, and a mountain coaster. Similarly alpine is New Germany State Park, located between Big Savage Mountain and the Eastern Continental Divide along Meadow Mountain. It features diverse forests, trails, and a lake that is suitable for fishing, swimming, and paddling. The area was once called “The Maryland Alps” by newspaper reporters for its winter sports.
Back in town, the Casselman Inn was constructed in 1842. It offers both rooms in its historic inn as well as its affordable motel with numerous amenities. Its restaurant serves country food reminiscent of the Pennsylvania Dutch and Amish background of the owners. There is also a bakery and café. For art and history, the Spruce Forest Artisan Village offers visitors the opportunity to interact with artisans in their studios. Since a storm in 2020, the log cabins have been repaired, and more trees have been planted.
Chesapeake City
Chesapeake City is the only town in Maryland situated on a working commercial canal, the Chesapeake & Delaware Canal. At its completion in 1829, the town only had two structures. Now, Chesapeake City’s historic district is listed on the National Register of Historic Places, boasting historic homes, shops, and galleries with a distinct Victorian charm. The Ben Cardin C&D Canal Trail follows the canal from end to end, all the way to Delaware City. The C&D Canal Museum offers a detailed history with interactive displays and items of interest for all ages.
Schaefer’s Canal House is the only restaurant on the north side of the canal. It features a full bar and dining experience, while the outside deck and tiki bar open in warmer months. Schaefer’s is also equipped to service guests overnight at its marina, whether mega yachts or local transit boaters. Also located on the waterfront is Pell Gardens downtown. It was designed by John Paul and Veronica Lucas, who also designed the Korean War Memorial on the National Mall in Washington.
Oakland
Oakland is surrounded by mountains, valleys, forests, and waterfalls. Nine miles north of town is Swallow Falls State Park with rocky gorges, rapids, and hemlock woods. A 1.25-mile trail takes hikers through Swallow Falls. Equally of interest is downtown Oakland, with its pedestrian-friendly shopping, restaurants, and historical sites, including the Oakland B&O Museum. Built in 1884, it is one of the nation’s best examples of Queen Anne railroad architecture. Tours and exhibits are available at the station as well as on the Baldwin Engine and Caboose.
Oakland also has its share of scenery within town, as found at Broadford Lake Park. It offers rentable charcoal grills, pavilions, a lake with a beach for swimming, sports courts, and paddle boat rentals. It hosts celebrations for holidays throughout the year. Oakland is also home to the Garrett County Arts Council, where visitors can stop by The Gallery Shop for a variety of handcrafted items, including paintings, photographs, pottery, blown glass, and more. It currently displays artwork from more than 100 artisans.
Beauty From Mountains To Chesapeake Bay
Maryland’s small towns reflect the state’s diversity, stretching from alpine landscapes in Grantsville to coastal charm in Berlin and maritime heritage in St. Michaels. Each community’s history, scenery, and culture are as abundant as the blue crabs that define the Chesapeake. Whether through waterfalls, vineyards, lighthouses, or artisan villages, they form a mosaic of experiences that highlight the state’s beauty. Maryland appeals to numerous senses of what beautiful truly is, with influences ranging from the Bay to the mountains.
