Ocean City, Maryland, USA. Boardwalk.Editorial credit: Yeilyn Channell / Shutterstock.com

The Best Small Towns in Maryland for a Weekend Retreat

Maryland is an exceptional destination among the Southern states, known for its blue crabs, captivating Civil War heritage, and picturesque natural scenery. While the state is known for large cities like Baltimore, it is also home to a series of idyllic small towns that embody the true heart and soul of the Old Line State. Such cities lie across the various landscapes in Maryland, from the foothills of the Blue Ridge Mountains to the shores of the Chesapeake Bay.

On the outskirts of the major thoroughfares are countless appealing communities that come alive on weekends with their historic charm, recreational opportunities, and small-town hospitality. From waterfront hamlets to mountain villages, escaping to these scenic towns in Maryland promises a relaxing retreat immersed in beauty, heritage, and community spirit.

St. Michaels

Street view of shops and restaurants in the historic downtown of St. Michaels, Maryland, USA.

The historic downtown of St. Michaels, Maryland, USA. Editorial credit: MeanderingMoments / Shutterstock.com

This picturesque waterfront town along the Chesapeake Bay charms visitors with cozy coastal scenery, beautiful marinas, historic downtown, and a delectable seafood scene. Since the city’s founding in 1672, St. Michaels has served as a vital seaport and maintains a storied nautical heritage, well documented at the Chesapeake Bay Maritime Museum. The facility keeps a collection of interactive exhibits featuring artifacts, old vessels, and other relics detailing seafaring exploits on the Chesapeake Bay. Several local outfitters present visitors with the opportunity to experience the town's beauty from the water during a tranquil sailing trip, including St. Michaels Harbor Shuttle.

The bustling wine and dining scene means your trip will only be complete after sampling the area's delectable cuisine. Stars Restaurant serves delicious dishes prepared with fresh ingredients from Maryland's Eastern Shore. Finally, the town has plenty of lodging areas, with top-rated hotels like St. Michaels Harbor Inn promising travelers a comfortable night's sleep.


Historic downtown Berlin in Maryland, USA, featuring brick buildings, hotels, and small shops catering to tourists.

Historic downtown Berlin in Maryland, USA. Editorial credit: Kosoff / Shutterstock.com

Berlin is a precious gem on Maryland's Eastern Shore, famous for its Victorian town center, where rows of historic homes and exciting museums guarantee vacationers a soothing journey into the bygone eras. Walking through the tree-lined streets in downtown Berlin exposes you to a selection of historical markers worthy of attention. The Calvin B. Taylor House is an exciting example; constructed in 1832, it offers a window into Victorian-era Berlin by displaying a range of antiques, artifacts, and other memorabilia. The town hosts a cluster of bustling breweries, allowing visitors a taste of refreshing craft beers at establishments like Burley Oak Brewing Company.

Those looking to thrive in the outdoors will feel at home exploring Assateague State Park. This beautiful barrier island bordering the Atlantic Oceans is home to sandy shores, where herds of wild ponies roam free. Tourists have little to worry about accommodation, with several hotels, including the Atlantic Hotel, delivering a rustic lodging experience in the heart of downtown.


Cumberland, Maryland, featuring a church in the city/town.

Cumberland, Maryland, featuring a church in the city/town.

Spend an adventurous weekend discovering the Allegheny Mountains scenery within this small community. Cumberland boasts a rich railway heritage, serving as a prominent transportation hub in the 19th century. A tour of the Allegany Museum offers newcomers a detailed town history lesson while exposing them to a vast collection of around 50,000 artifacts. Meanwhile, the best way to take in the mountain scenery surrounding Cumberland is to hop aboard the Western Maryland Scenic Railroad for a relaxed sightseeing excursion inside an old steam locomotive.

Downtown Cumberland is a quaint neighborhood perfect for exploration on foot. It harbors several points of interest worth checking out. If you appreciate the arts, you can catch a live show at the Cumberland Theatre, alongside the locals in a family-friendly atmosphere. Finally, Hampton Inn Cumberland is among the top-rated area hotels for those looking for a remarkable accommodation experience.

Havre De Grace

Warm cloudy day on the boardwalk in Havre de Grace, Maryland.

Warm cloudy day on the boardwalk in Havre de Grace, Maryland.

Havre de Grace is an embodiment of the charm of coastal living offered by the tiny towns in Maryland. Set on the confluence of the Susquehanna River and the Chesapeake Bay, this adorable community presents relaxed open spaces with beautiful water views. Tourists get a soothing feeling simply by strolling down the Havre de Grace Promenade, which features an isolated setting and unrivaled vistas of the Susquehanna River. For the best photo opportunities in town, you can visit the Friends-Concord Point Lighthouse. This iconic landmark dates back to 1827 and puts you at a vantage point to capture the best scenes of the ocean.

Havre de Grace is home to multiple museums documenting various aspects of its storied heritage. At the Havre de Grace Maritime, tourists can get familiar with the town's nautical history, with a focus on economic practices like crabbing and fishing. When it is time to call it a day after hours of discovering the town, you can book a room at the luxurious Vandiver Inn.


Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland, USA.

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland, USA.

This tiny Kent County community is known for its vibrant art scene and hosts Maryland's second-largest cluster of restored 18th-century homes. Chestertown's colorful heritage comes to life inside the Historical Society of Kent County. Set in the heart of the historic district, the venue exhibits a portfolio of artifacts that not only preserve the town's past but also that of the entire county. Chestertown's rich arts community is shown through the presence of one of the nation's oldest liberal arts colleges, Washington College. Expectedly, several art centers dot the town, highlighted by the Garfield Center for the Arts.

Every Saturday, Chestertown hosts a lively Farmer's Market, bringing together vendors and shoppers for a pleasant day of trade with farm-fresh produce and unique handcrafts on the menu. After a fulfilling day exploring the town, travelers can take advantage of the affordable yet cozy accommodations offered by the Driftwood Inn.

Ocean City

Wide aerial shot of Ocean City, Maryland, looking north at sunrise.

Wide aerial shot of Ocean City, Maryland, looking north at sunrise.

A weekend on the sandy shores of the Atlantic Ocean always makes for a remarkable retreat. Ocean City presents the perfect atmosphere for those looking to escape the crowds and enjoy quality alone time by the beach. Its idyllic open spaces, such as Ocean City Beach, are perfect for unwinding and meditation while soaking up sun rays. With this, a stroll along the Ocean City Boardwalk allows you to take in the scenic views of the Atlantic. The promenade features a bustling mix of businesses with souvenir shops, small eateries, and outdoor performers, creating a rich social atmosphere.

Take advantage of the opportunity to explore the open sea for an adrenaline-filled excursion courtesy of West OC Watersports. The local outfitter offers hire services for different vessels, allowing tourists to enjoy exciting fishing, tubing, jet skiing, and other fun adventures. Ocean City has plenty of hotels, and some top-rated options include Holiday Inn & Suites and Ocean 1 Hotel & Suites.


Street view of Hagerstown, Maryland, USA.

Street view of Hagerstown, Maryland, USA.

Hagerstown provides visitors with an excellent opportunity to celebrate historical and cultural heritage with an impressive collection of museums. The town hosts a fair share of interesting venues for history buffs and culture vultures, including the Washington County Museum of Fine Arts. The venue houses a permanent collection of intricate artworks, ranging from paintings and sculptures to drawings. The Hagerstown Roundhouse Museum is another worthwhile destination, showcasing local railroad heritage through model train exhibits and related artifacts.

Beyond the exciting museums, Hagerstown has alternative pursuits, such as enjoying an immersive cultural experience at the Pennsylvania Dutch Market. Visitors taste unique Amish culture by shopping for authentic handmade crafts and sampling tasty Amish cuisine. Lastly, remember to check into the Hampton Inn Hagerstown for comfortable night stays in the town.

Embrace the Charm of Maryland's Small Towns

While Maryland's top cities offer abundant amenities and culture, taking a weekend to soak in the laid-back atmosphere of these exquisite small towns in the backcountry ensures a most memorable respite. Their scenic settings, preserved heritage, and community spirit invite fulfilling exploration at a leisurely pace. Whether strolling historic streets, waterfront boardwalks, or nature trails, escaping to any of the above small towns in Maryland immerses visitors in the authentic charms of the Old Line State away from the choking crowds.

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