10 Top-Rated Small Towns In Maryland
Beyond famous cities like Baltimore and Frederick, Maryland has adorable small towns removed from the busy metro areas. Despite being overlooked, they harbor rich cultural and historical heritages that cumulatively tell the story of the Old Line State. When you are tired of the chaos and commotion of urban living, these laidback locations present the ideal escape while promising tons of fun activities. From the Appalachian Mountains peaks and the Chesapeake Bay waterfront to the Susquehanna River banks, they offer an easygoing pace of life with access to innumerable outdoor opportunities. Each town has a distinct personality and vibe, promising a unique experience wherever you choose. Whether you are a history buff, culinary connoisseur, art lover, or outdoor adventurer, these top towns in Maryland should be on your travel checklist.
St. Michaels
St. Michaels tops many best “small towns” lists in the state and nation due to its impressively preserved historic district, scenic Chesapeake Bay scenery, and sumptuous Maryland crab cuisine. With a history dating back to the mid-1600s, the town harbors a treasure trove of historic sites. You can learn about the region’s nautical heritage at the Chesapeake Bay Maritime Museum. But for a broader look at the town’s colorful past, St. Michaels Museum promises an immersive experience in the heart of the town. It even schedules walking tours for guests through all the top historic sites in the town. The Chesapeake Bay makes for idyllic outdoor scenery in St. Michael’s, featuring spectacular water views and fresh sea breeze. You can make the most of this at the St. Michaels Marina, which provides plenty of aquatic fun. Lastly, your trip is incomplete without sampling the town’s famous seafood. The Crab Claw is one of the best seafood joints in the region and guarantees to tickle your taste buds with delicious crab dishes.
Cumberland
Picturesque riverside trails, superb mountain views, and numerous historical markers draw visitors to this small Allegheny County town. Cumberland’s prominence came to the fore in the 19th century as a transportation center. You can get a sense of this heritage aboard the Western Maryland Scenic Railroad, which takes visitors on an unforgettable trip through the town’s wilderness, revealing the beauty of the Allegheny Mountains. Historians will have a full plate inside the Allegheny Museum, perusing over 50,000 artifacts depicting the history of the county, some dating back to the Native American settlement eras.
Meanwhile, Riverside Park provides an urban oasis for people to relax in a calm environment. Within the park lies George Washington’s Headquarters, a historic log cabin that once served as a command post for America’s first president. Lastly, fans of live performances can catch an entertaining show at the Cumberland Theater, from musicals and concerts to plays and dramas.
Cambridge
This picturesque coastal community on Maryland’s Eastern Shore exudes rich maritime heritage, with opportunities to get on the water. Its rich history intertwines with the life and times of the legendary Harriet Tubman, immortalized at the Harriet Tubman Museum and Educational Center. Inside the facility, you can browse various artifacts and watch a short recording of historical events like the Underground Railway and the Civil War. Furthermore, Richardson Maritime Museum lets you relive over three centuries of nautical history by inspecting artifacts dedicated to Eastern Shore boat building culture.
Visitors can enjoy the best views in town while strolling along Long Wharf Park. Its laid back setting features spectacular water vistas and picnic areas, perfect for unwinding and watching the sunset. Finally, those curious to get on the water can rent a vessel from the Dorchester Skipjack Committee for a sightseeing excursion from the water.
Chestertown
Chestertown stands out for the colonial architecture in its historic district. Wandering the quaint streets of Chestertown Historic District is like stepping back in time, with restored 18th-century homes offering a window into the bygone eras. A stop at the Historical Society of Kent County lets you explore an exciting collection of artifacts and memorabilia chronicling the region’s rich past. Meanwhile, Sumner Hall looks at African American life in Chestertown in the early 20th century.
The local arts and culture scene is nothing to scoff at, with the town hosting several art centers and venues. If you enjoy theater, you can catch an entertaining live performance at the Garfield Center for the Arts, which stages musicals, plays, concerts, and other community events. But for a more immersive cultural experience, consider shopping at the Chestertown Farmers Market. It is a chance to mingle with the townsfolk and sample their farm-fresh produce, from herbs and fruits to vegetables, in a festive atmosphere.
Berlin
Berlin might be a small town, hosting just about 5,000 residents, but it is jam-packed with touristy delights that will impress all types of travelers. From museums to parks and art galleries, it has something for everyone. Beachgoers can’t miss out on Assateague State Park, which boasts a white sand beach and clear Atlantic Ocean waters. The park is unique for a herd of wild horses that can be seen wandering the shoreline. On the other hand, historians will prefer visiting the Calvin B. Taylor House, a 19th-century homestead with a unique Federal-style construction exhibiting artifacts and various other local memorabilia.
Berlin has its fair share of quirky attractions, and the Mermaid Museum will leave you scratching your head. Located in the heart of the town, the facility displays everything mermaid, blending local legends, history, and pop culture, After a long day exploring the top sites, try unwinding with a glass of freshly crafted wine at the Windmill Creek Vineyard & Winery accompanied by great food and live music.
Havre De Grace
This scenic waterfront town provides unprecedented water views, interesting museums, and beautiful parks. It sits where the Chesapeake Bay and the Susquehanna River meet and boasts a rich nautical heritage that you can learn about at the Havre de Grace Maritime Museum. Housed inside are artifacts and exhibits focusing on local fishing and crabbing history. Also, the Friends-Concord Point Lighthouse is an iconic town landmark that takes you back to the early 1800s. It was constructed to warn vessels of the treacherous bay waters and schedules educational tours for the public.
Havre de Grace has lovely outdoor opportunities at the Susquehanna State Park, such as fishing, camping, boating, and hiking. The park features a campground with almost 70 sites for those looking for the ultimate outdoor experience. Alternatively, you can opt for a lazy stroll along the Havre de Grace Promenade to soak in the Atlantic views and spot different species of shorebirds.
Mount Airy
This delightful Western Maryland locale has been praised for its beautiful countryside and trademark Southern hospitality. It welcomes wine and beer lovers to sample freshly crafted drinks in its multiple breweries and wineries. Black Ankle Vineyards is an excellent place to start, surrounded by the rolling foothills of the Appalachians. Here, guests enjoy a fun guided tour of the property with a stop at the tasting room and the opportunity to picnic. For beer chuggers, the Milkhouse Brewery serves handcrafted brews that you can enjoy while admiring local art.
Mount Airy has one of the best countryside scenery in Maryland, and nature lovers will relish a tour of the Audrey Carroll Audubon Sanctuary. Stretching more than 100 acres, this cozy nature space houses a diverse ecosystem featuring 155 different bird species and wildlife. The best time to visit the sanctuary is in spring or fall, during monarch butterfly tagging and bird migration.
La Plata
La Plata is easily one of the most charismatic towns in Maryland, delivering laidback vibes with its simple way of life. It has the perfect rural scenery to escape city life's rigors. A small business Mecca, the town is famous for the numerous family-owned shops and restaurants dotting its town center. Tourists can look forward to a rich cultural experience, especially at the La Plata Farmers Market. The market brings together vendors from across Southern Maryland to sell farm-fresh produce, baked goods, local wine, and various handcrafted souvenirs.
But if you don’t make it on market day, you can stop by Marie’s Diner for a piece of the experience by sampling delicious comfort foods in a family-friendly atmosphere. La Plata houses several historic sites worth checking out, including the La Plata Firehouse Museum, which documents the town’s firefighting heritage. You can follow this up with a tour of the La Plata Train Station Museum to browse vintage exhibits and artifacts showcasing local railroad history.
New Market
Dubbed “Antique Capital of the World,” New Market provides treasure hunters with the chance to leave with rare finds. It harbors a mix of antique shops throughout the town center, including Robert Esterly Antiques, selling all types of souvenir items, from 18th-century furniture and pottery to décor art and glassware. If you are not a collector, you can try strolling through the New Market Historic District. Designated a National Historic Landmark, it features well-preserved old-world structures, some dating back to the 1700s, offering a glimpse into pre-Victorian and Victorian-era New Market. New Market has a thriving wine scene, evidenced by multiple craft wineries in the town. If you fancy a taste of fine wine, you can visit New Market Plains Vineyards and choose from red, white, cider, and fruit varieties. Finally, one of the best times to visit the town is during the Christmas in New Market Celebrations, which feature a grand parade, beautiful decorations, lots of food, and endless fun.
Salisbury
Along Maryland's eastern shore lies the charming small town of Salisbury, where history, nature, and local flavor harmoniously blend. Outdoor enthusiasts will find tranquil spaces around every turn. The 262-acre Pemberton Historical Park invites adventurers to explore its 4.5 miles of wooded trails passing through scenic surroundings. Meanwhile, Salisbury Zoological Park packs diversity into its compact 12 acres, housing exotic species from across the globe. Young nature lovers will be delighted by the chance to interact with playful sloths, majestic jaguars and lumbering bears up close.
Steeped in architectural heritage, the 1805 Poplar Hill Mansion transports visitors back to the early Federal period through ornate furnishings and details that are still intact today. When hunger calls, a cozy harborfront restaurant, Morgan's Oyster House, awaits with its signature seafood dishes - savor creamy crab cakes, sweet oysters, and local shrimp alongside scenic coastal views.
Final Thoughts
There is no shortage of fun adventures to keep you entertained in the small towns in Maryland. From the rolling Allegheny Mountains of Cumberland to the picturesque Chesapeake Bay in St. Michaels, they showcase the charming diversity in this lovely Mid-Atlantic state. Whether you are looking for an exciting lesson in history, an immersive cultural experience, or a thrill in the great outdoors, you won’t run out of options that will dance to your tune. The chill atmosphere of an authentic small-town vibe awaits all who venture off the beaten path to discover these highly-rated hidden gems.
