8 Adorable Small Towns In Maryland
Maryland almost has it all! Between its gorgeous natural landscapes, immersive cultural heritage, scrumptious seafood, and nostalgic historical sites, tourists can expect an all-around experience. Add to this a touch of authentic Southern hospitality, and you get one of the best destinations along the East Coast. Whether planning a weekend escape or a seasonal vacation, the state offers stunning towns that cater to every kind of traveler.
From waterfront gems like St. Michaels, framed by quiet marinas, to postcard-worthy mountain towns like Thurmont, riddled with scenic wilderness trails, these small communities capture Maryland’s charm in its purest form. If you are searching for destinations that boast tranquility, character, and adventure, these adorable small towns in Maryland deliver unforgettable moments at every turn.
St. Michaels
St. Michaels is a lovely Chesapeake Bay village on the Eastern Shore, renowned for its beautiful marinas, seafood spots, and historic district. The Chesapeake Bay Maritime Museum is a significant heritage venue in downtown St. Michaels, showcasing the region's rich nautical history through a diverse collection of artifacts, relics, and historic vessels spanning an 18-acre campus.
Quaint waterfront restaurants in town welcome vacationers to savor delicious local seafood. Foxy's Harbor Grille is one of the go-to spots for visitors and serves homemade crab cakes and steamed seafood, accompanied by finely crafted local beers. The outdoor inclined often head to Muskrat Park, where a small but tranquil green space lets them relax and revel in majestic harbor views.
Havre De Grace
Situated dramatically where the Susquehanna River meets the Chesapeake Bay, Havre de Grace is a picturesque waterfront town with a rich maritime heritage and a vibrant entertainment district. A walk down the Havre de Grace Promenade places you in the best spot to admire the town's unique beauty. The pleasant boardwalk connects to Millard Tydings Memorial Park, which provides 22 acres of serenity, where you can sit for a picnic and watch the day go by.
Historic downtown Havre de Grace welcomes newcomers to learn about the early days of commercial crabbing and fishing at the Havre de Grace Maritime Museum. This boasts a dynamic selection of artifacts and archives, highlighting maritime skills, environment, and culture. Furthermore, live entertainment is accessible at the Cultural Center at the Opera House, featuring a lineup of invigorating theatrical performances.
Ocean City
Sandy beaches, world-class amusement parks, and unforgettable festivals bring tourists to this popular resort community on the Atlantic Coast. Ocean City is a hub for summer travelers, inviting vacationers to let loose while soaking in the sun and taking in the stunning ocean views from the sandy acres of Ocean City Beach. This 10-mile stretch of shoreline offers the perfect atmosphere for sunbathing, swimming, and picnicking. It also provides ready access to the Ocean City Boardwalk, where everyone comes together to shop, sample the roadside fare, stroll, play, and have a fun time with fellow tourists and locals.
Ocean City also excites vacationing families with delightful amusement venues, highlighted by Jolly Roger Amusement Park. This amusement park features a Ferris wheel, thrill rides, arcade games, go-karts, and much more to entertain visitors of all ages. Finally, there is always something festive happening in the town, thanks to a loaded event calendar, featuring events like the Ocean City Sunfest.
Crisfield
Popularly known as the "Seafood Capital," this adorable Chesapeake Bay town invites tourists to indulge in its delicious seafood and sail on its calm waters during a low-key staycation on the Eastern Shore. Crisfield is home to several marinas, including Somers Cove Marina, where watersports lovers can rent a vessel to access the open sea. Thanks to Tangier Island Cruises, romantic sails on the Chesapeake Bay await, allowing newcomers to fully appreciate the region's beauty en route to the nearby Tangier Island.
The Crisfield Heritage Foundation documents and shares the community's dynamic and diverse history through educational tours that enable guests to browse historic items. Although Crisfield can be sleepy at times, it definitely comes alive during the National Hard Crab Derby, which brings festivalgoers together for fresh seafood, games, competitions, and family-friendly fun.
Thurmont
Thurmont is a mountainous escape near the Pennsylvania border, renowned for its exquisite natural landscapes, which serve as a playground for stimulating outdoor adventures. The town's long list of park areas includes Cunningham Falls State Park. This heavenly oasis stuns first-timers with its cascading 78-foot waterfall, while providing swimming, picnicking, hiking, and nature photography opportunities. The Catoctin Wildlife Preserve offers a memorable experience for animal lovers, where they can interact intimately with exotic wildlife species in a lovely 100-acre zoo.
History lovers will enjoy inspecting the Roddy Road Covered Bridge, a picturesque portal to the mid-19th century, preserving old-world engineering. Finally, oenophiles are welcome to taste delicious local wines in the foothills of the Blue Ridge Mountains by touring the Catoctin Breeze Vineyard.
Cumberland
Cumberland is an exquisite getaway to the Allegheny Mountains of Western Maryland, steeped in natural beauty and home to a walkable historic downtown. Those drawn by the dramatic surroundings can ride the Western Maryland Scenic Railroad for a time-lapse of the scenery as the vintage locomotive cuts through the countryside. Alternatively, you can hop on a bike for a spectacular excursion along the Great Allegheny Passage to witness the allure of Pennsylvania's Laurel Highlands.
Besides the great outdoors, Cumberland offers a glimpse into life in the Victorian era at the Gordon-Roberts House, which preserves the home of a famous local attorney and features furnishings from the late 19th century. Additionally, the town square is renowned for its delicious eats, tantalizing the taste buds with mouth-watering Cajun fare at Baltimore Street Grill.
Oakland
A trip to this Garrett County village takes you to the state's highest elevations, placing you at a vantage point to admire one of the most adorable small towns in Maryland. Oakland is renowned for its pristine beauty, best exemplified by Swallow Falls State Park. This natural playground attracts hikers, bikers, campers, and swimmers, featuring a magical 54-foot waterfall with access to the Youghiogheny River. For families exploring the outdoors, Alpaca Acres Farm and Fun offers a more suitable getaway, with the opportunity to pet and feed gentle alpacas and play with the kids inside a corn maze.
Those interested in the community's past can learn about its transportation history at the Garrett County Museum of Transportation, which features a collection of exhibits ranging from vintage buggies and carriages to sleighs and a sailboat.
Chestertown
Chestertown is a colonial town on the Chester River, offering a unique mix of unmatched historical heritage, a lively performing arts scene, and family-friendly river adventures. Its historic district features brick-lined streets with vintage mansions that reflect its enduring heritage, and first-timers can gain an overview of the community's history at the Historical Society of Kent County. Meanwhile, residents have an undying appreciation for the arts, with many finding time to support local artists by watching plays, concerts, and other productions at the Garfield Center for the Arts.
Guests are also welcome to experience Chestertown from the water during a leisurely, scenic cruise offered by the Chester River Packet Company. If you find yourself in a position to visit around May, be sure to attend the famous Chestertown Tea Party Festival for an unforgettable cultural experience.
Between the foothills of the Allegheny Mountains in Cumberland and the sand-swept shores of the Atlantic Coast in Ocean City, these adorable small towns in Maryland paint a portrait of charm, history, and natural beauty in the United States. Whether exploring oceanside escapes, mountain hideaways, riverfront enclaves, or historic settlements, these hidden gems spoil tourists with novel experiences that lead to lasting memories, proving that some of the state’s greatest treasures come in the smallest packages.
