View of historic buildings in the town of Chestertown, Maryland. Image credit EQRoy via Shutterstock

9 Most Beautiful Small Towns In Maryland You Should Visit

Maryland's most charming and underappreciated assets are its little towns, which fascinate travelers with their maritime history. These villages are tucked away like hidden pearls within the state's expansive landscapes. This state treats its fans with diverse views, from the tranquil Chesapeake Bay to the beautiful Appalachian Mountains. Maryland's little towns provide a true retreat from the every day, whether visitors find themselves meandering along cobblestone streets dotted with ancient buildings or indulging in locally grown treats at small farmer's markets. Creative spirits will find inspiration in scenic settings where vivid colors dance over nature's canvas. These are the most beautiful small towns of Maryland you should visit to cherish the simplicity and genuineness of the locals and discover the authentic beauty of Maryland.

Best Small Towns In Maryland To Chill OutWelcome to Maryland, a state brimming with charming miniature towns where you can break away from the rush of urban life and relish the serenity of the outdoors.

Berlin

Wild ponies grazing on marsh vegetation in late winter at Assateague Island National Seashore on the Atlantic Ocean in Berlin, Maryland, USA.
Wild ponies grazing on marsh vegetation in late winter at Assateague Island National Seashore on the Atlantic Ocean in Berlin, Maryland.

Berlin is a beautiful town that beckons visitors with its timeless charm and warm hospitality along Maryland's Eastern Shore. Known for its feral ponies, Assateague State Park is the perfect stop to try surfing, swimming, beachcombing, or checking out waterfowls and deers in the nearby marshes. Berlin's quaint boutiques, art galleries, notably the Art in The Fields and nearby Adcock Art Studio, and cozy cafes deliver an authentic small-town experience. Don't miss the Burley Oak Brewery, renowned for its handcrafted brews and inviting ambiance. 

Boonsboro

View of Boonsboro, Maryland, from South Mountain.
View of Boonsboro, Maryland, from South Mountain.

In the serene foothills of South Mountain rests Boonsboro, with its tranquil ambiance and breathtaking vistas. Head to the nearby Appalachian Trail for trekking and mountain biking or the Greenbrier State Park to take advantage of swimming, fishing, boating, and camping sites. Boonsboro's literary charm also attracts book lovers, thanks to its close association with famed author Nora Roberts. Delve into the world of literature at the iconic local bookstore, Turn the Page, which hosts regular author events and signings. 

Leonardtown

The view on the sidewalk from the window of the Social cafe on Main street in Leonardtown, Maryland.
Looking out from Social cafe on Main Street in Leonardtown, Maryland. Image credit Alexanderstock23 via Shutterstock

Perched along the Potomac River, Leonardtown exudes maritime charm and rich history. You can check out the nearby St. Clement's Island Museum, which commemorates the area's first European settlers. Art enthusiasts will find delight in the local galleries, such as Fenwick Street Used Books & Music, which promises an eclectic collection of artistic treasures. For a relaxing day by the water, Leonardtown Wharf Park is a haven with picturesque views and options for kayaking, boating, and enjoying the playground. Leonardtown's waterfront dining options, like The Front Porch, provide magnificent views and delectable culinary experiences. 

Hancock

Downtown Hancock, Maryland.
Downtown Hancock, Maryland. Image credit Alejandro Guzmani via Shutterstock

Hancock is a haven for outdoor enthusiasts seeking adventure and tranquility. The C&O Canal Towpath and Western Maryland Rail Trail converge here, inviting you to explore miles of scenic pathways to hike or bike. The town's rustic charm is evident at Buddy Lou's Eats Drinks and Antiques, where vintage shopping and delightful meals await. Head over to Fort Frederick State Park, featuring the namesake Fort in its heart, for history tours, picnics, boating, hiking, and camping. 

Chestertown

A little girl wearing pink casual clothing is sitting alone on a metal bench in the Fountain Park of Chestertown, Maryland
Fountain Park of Chestertown, Maryland.

The adorable town of Chestertown enchants travelers with its colonial architecture and vibrant arts scene. This waterfront town boasts a rich maritime heritage, evident at the Chestertown Waterfront and Custom House Marina. You can also stop by boutique stores, such as Twigs and Teacups, known for unique gifts and charming trinkets. With a vibrant arts scene, visitors can appreciate jazz performances, open mics, play adaptations, and more at the Garfield Center for the Arts or admire contemporary masterpieces at Massoni Art Gallery or Les Poissons Gallery. Don't miss the Farmers' Market, where vendors display an array of fresh produce and handcrafted goods. 

Cumberland

Aerial view of Cumberland, Maryland.
Aerial view of Cumberland, Maryland.

Cumberland stands as a gateway to Maryland's scenic western region in the Allegheny Mountains. Boasting a rich industrial heritage, this town invites history buffs to embark on scenic train rides with the Western Maryland Scenic Railroad and uncover tales of the Chesapeake and Ohio Canal at the C&O Canal National Historical Park Visitor Center. Rocky Gap State Park offers outdoor enthusiasts a paradise with hiking, fishing, and boating opportunities. Cumberland's downtown exudes a nostalgic charm with historic architecture, complemented by charming cafes and antique stores like Fort Cumberland Emporium. The Queen City Creamery is a must-visit for sweet treats and nostalgia-inducing ice cream parlor vibes. 

Kensington

Festival of Lights at the Washington, DC LDS Temple in Kensington, Maryland where 600,000 lights reflect and illuminate the grounds for public viewing.
Festival of Lights at the Washington, DC LDS Temple in Kensington, Maryland.

Montgomery County’s Kensington is a suburban oasis that balances the tranquility of a small town with the accessibility of urban amenities. Antique enthusiasts will delight in exploring unique finds at local shops like the Kensington Antique Row. Splurge an afternoon at the Kensington Farmers' Market, looking for fresh produce and artisanal products. For a cultural experience, the Kensington Arts Theatre hosts musical productions. The nearby Kensington's Rock Creek Park is your destination to hike through lush woodlands and meadows, gallop on the bridle paths, take a shot at the 18-hole golf course, and go paddling in Rock Creek.

Monkton

Monkton station in Maryland
Monkton station in Maryland.

Maryland's picturesque horse country is home to the cutesy town of Monkton, a haven for equestrian enthusiasts and nature lovers alike. The first stop has to be the nearby Gunpowder Falls State Park, offering hiking, fishing, and kayaking amidst pristine landscapes. A 20-minute drive will take you to Shawan Downs Steeplechase. Nature preserves like Ladew Topiary Gardens are a fan-favorite for visitors with their meticulously manicured beauty, whimsical topiaries, butterfly house, and magnificent Manor House. Monkton's country stores and farm stands, like Manor Tavern, provide a taste of locally-produced delights.

Bel Air

South main street in Bel Air, Maryland
South main street in Bel Air, Maryland. Image credit Yaoiloverr Yaoiloverr, CC BY-SA 4.0 via Wikimedia Commons

The vibrant and charming Bel Air balances modern convenience with its historic roots. Head to the Liriodendron Mansion, a stately estate offering a glimpse into the town's past and hosting art exhibitions, concerts, and cultural events. Bel Air's community-oriented spirit is evident in events like the Maryland State BBQ Bash, drawing crowds with its delectable barbecue, live bands, and championships, including Tailgate Challenge and KCBS Championship Competition. The Bel Air Farmers' Market, featuring local vendors and artisans, is your stop for some handcrafted goodies. Ma & Pa Trail, a former railroad line, invites you to hike and cycle through picturesque landscapes.

Most Underrated Towns In MarylandMaryland is chock full of history and culture, as well as beauty and charm, which makes it worth the visit.

Every small town in Maryland boasts a unique character, enriched by its historical significance, artistic appeal, and stunning natural landscapes. From the maritime allure of Leonardtown along the Potomac River to the tranquil charm of Monkton amidst picturesque horse country, Maryland's small towns offer an authentic escape from the fast-paced world.

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Rajender Bhatia August 16 2023 in Places

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