![View of Chesapeake City, Maryland.](/upload/94/05/13/md.jpg)
11 Stunning Small Towns In Maryland
Maryland's winning blend of rich historical heritage, beautiful outdoor landscapes, and a mix of Northern and Southern cultures make it a prime destination along the East Coast. Although it houses bustling metropolises like Baltimore and Frederick, it is also home to select small towns in the backcountry areas that feel a world apart from the big cities, with thinner crowds, a slower pace of life, lovely natural settings, and close-knit communities.
As such, they provide the perfect rural getaway to unwind and bask in simple life pleasures. Together, they represent the lifeblood of the Old Line State, harboring hidden histories and unique cultures that showcase its authentic character and personality. From beachside enclaves like St. Michaels to mountain havens like Thurmont, these stunning small towns in Maryland ought to be on your next travel itinerary.
Boonsboro
![Boonsboro, Maryland.](/r/w768/upload/1e/6d/f7/downtown-boonsboro-maryland.jpg)
Boonsboro lies in the foothills of the South Mountain and boasts stunning natural scenery that complements its rich history. This leaves endless outdoor opportunities across its vast nature areas, including Greenbrier State Park. The pleasant space has a 42-acre reservoir with a sandy beach surrounded by lush forests, cultivating recreational activities like swimming, camping, hiking, canoeing, and hunting. Boonsboro also provides access to the Appalachian Trail in the South Mountain State Park. Scenic overlooks at High Rock and Weverton Cliffs reward hikers with breathtaking panoramas of the surrounding landscapes.
If you are not immersing in the great outdoors, you might find interest in the past at the Boonsborough Museum of History. This resourceful venue documents the town's dynamic history since its founding in 1792 and holds a collection of Civil War relics, ancient artifacts, weapons, glassware, and similar memorabilia.
Bel Air
![Downtown Bel Air, Maryland.](/r/w768/upload/20/f5/46/bel-air-downtown.jpg)
This delightful town in Harford County wears many hats; it is a historical hub, an outdoor haven, and a little gastronomy mecca. Bel Air harbors a decent share of vintage landmarks and markers, such as the Liriodendron Mansion, which transports vacationers back to the 19th century. Constructed in the 1890s, this opulent home sports distinct Palladian architecture and belonged to Dr. Howard Kelly and his wife.
Approximately 50 eateries and restaurants in Bel Air hint at its vibrant and diverse culinary scene. Foodies can enjoy New American dishes at One Eleven Main or delicious Mexican cuisine at Mucho Gusto Bel Air. Finally, extroverted tourists can find a nice spot to fit in at Bynum Run Park. This tranquil oasis with quiet walking trails and a sandy beach provides the perfect setting to relax and let your mind wander.
Chesapeake City
![A scenic view of Chesapeake City, Maryland.](/r/w768/upload/22/6e/0b/shutterstock-231782263.jpg)
This tiny Chesapeake Bay community is known for its unmatched water views, rich historical heritage, and sumptuous seafood scene. Several museums help preserve its dynamic past, with the Chesapeake City Museum inviting newcomers to familiarize themselves with its unique background. The venue showcases a comprehensive collection of old photographs, books, documents, archives, newspapers, and other memorabilia taken from the community over the years. Multiple boat tour operators, including M/V Summer Breeze, allow guests to enjoy the beautiful local scenery from the water during a laid-back cruise.
![Chesapeake City, Maryland.](/r/w768/upload/b0/db/db/chesapeake-city-maryland-scene-c.jpg)
Lastly, your trip can't be complete without sampling the famous Chesapeake Bay cuisine, readily accessible by the Bayard House Restaurant. This rustic diner, housed inside an 18th-century house, serves delicious seafood like fresh-shucked oysters and the trademark Maryland crab cakes.
Cumberland
![A scenic view from a hill overlooking the historic town of Cumberland, Maryland.](/r/w768/upload/fa/50/dc/shutterstock-2459945321.jpg)
This rural escape in the mountains of western Maryland boasts some of the most stunning views in the region, making it a haven for outdoor lovers. A ride on the Western Maryland Scenic Railroad offers the best way to soak up the scenes as the vintage locomotive drags through mountainous landscapes. Just like its nature, Cumberland charms visitors with its curious history. Among its numerous markers and sites, the Gordon-Roberts House stands out for preserving original artifacts. The house museum dates back to 1867 and stores various clothing, art, furnishings, toys, and other relics depicting Victorian-era life.
![Fall colors in Cumberland, Maryland.](/r/w768/upload/4c/c1/71/shutterstock-2515477557.jpg)
Furthermore, Cumberland maintains a vibrant creative scene and invites performance art lovers to riveting live shows at the Cumberland Theatre. The local hub stages dramas, plays, musicals, and similar productions for the public's amusement.
Chestertown
![Chestertown, Maryland.](/r/w768/upload/c0/ad/c9/shutterstock-1768100474.jpg)
Chestertown is a charming village on the banks of the Chester River, reputed for its well-preserved history and bustling cultural scene. It houses the Chestertown Arts and Entertainment District, where guests can get inspired by interactions with a colorful arts community. The Garfield Center for the Arts is where people gather to watch engaging musical and theatrical productions and support budding local talent. Meanwhile, MassoniArt Gallery exhibits beautiful works by artists of regional and national stature.
![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland, USA.](/r/w768/upload/f1/6a/bd/shutterstock-1686851782.jpg)
For those curious about the past, the Historical Society of Kent County chronologically documents the area's history through a vast stockpile of artifacts, relics, and memorabilia. It is the best place to trace Chestertown's evolution through the years since its founding in the early 1700s.
Kensington
![Kensington Train Station in Maryland.](/r/w768/upload/99/e0/53/shutterstock-2309084051.jpg)
Kensington is a short day trip away from Washington, D.C., and makes for a proper escape for those who appreciate relaxed, natural settings. The small town boasts a network of green spaces that let you reconnect with Mother Nature, including Clum-Kennedy Park. This spreads over an acre with a cluster of old-growth azalea, boxwood, and lilac trees, providing a shaded, quiet setting for picnickers and lazy strollers. The atmosphere is similarly soothing at Kensington Heights Park, which provides a family-friendly green space with amenities like a playground, picnic tables, and trails.
![Kensington Town Hall.](/r/w768/upload/38/7e/c5/kensington-town-hall.jpg)
Antique lovers and souvenir collectors have much to look forward to in Kensington. They can stop at Kensington Antique Row to check out its variety of vintage items, classical finds, and rustic collectibles.
Lexington Park
![Patuxent River Naval Air Museum.](/r/w768/upload/20/f1/1b/pax-river-museum-md1.jpg)
Lexington Park is a small community steeped in naval heritage and harbors an impressive network of nature spots. The town traces its beginnings to the founding of the Patuxent Naval Air Station at the height of the Second World War. This heritage has been preserved at the Patuxent River Naval Air Museum, which stores aircraft-related artifacts depicting aviation research by the U.S. Navy.
There is no shortage of parks in Lexington Park. When you need an outdoor escape, consider heading to John G. Lancaster Park for a quiet time in the open. Alternatively, you might be more impressed by Elm's Beach Park, which boasts an over 500-foot shoreline with a white sand beach. The spot is ideal for sunbathing, swimming, and enjoying stunning water views.
Monkton
![The Historic Monkton Railroad Station, Maryland.](/r/w768/upload/ba/c3/c1/shutterstock-2401925597.jpg)
Monkton provides the ideal escape from the crowded streets of neighboring Baltimore, known for its peaceful natural environment and a cluster of gorgeous historic homes. It is home to Manor Mill, a pre-revolutionary grist mill that was transformed into an art center. Today, it houses a fine art gallery and performance venue where enthusiasts watch musical shows. The Monkton Railroad Station presents a unique look into the railway heritage from the 19th century.
For the ideal rural experience, spare a few minutes to visit Inverness Brewing. The lovely establishment serves great-tasting craft beers in barn bars alongside farm food, giving patrons a taste of farm life in rural Maryland.
St. Michaels
![Downtown street in St. Michaels, Maryland.](/r/w768/upload/38/65/7b/shutterstock-2485457391-1.jpg)
St. Michaels is often ranked among the best small towns in Maryland for its picturesque Chesapeake Bay views, trademark Maryland crab dishes, and well-preserved historic district. With a heritage going back to the 17th century, St. Michaels is steeped in history and portrays its maritime exploits over the years at the Chesapeake Bay Maritime Museum. This has a cluster of interactive exhibits and relics related to regional nautical heritage. Meanwhile, St. Michaels Museum delves deeper into the community's history in a 19th-century structure with notable relics and memorabilia.
![Waterfront buildings in the town of St. Michaels, Maryland.](/r/w768/upload/bd/67/a0/shutterstock-1469479781.jpg)
Those willing to get out at sea can find several local outfitters at the St. Michaels Marina for pleasant cruises to explore the sights and sounds. Lastly, don't leave without trying the town's famous seafood at Bistro St. Michaels.
Havre De Grace
![Aerial sunset panorama of Havre De Grace, Harford County, Maryland, United States.](/r/w768/upload/d4/9a/45/sunset-panorama-havre-de-grace-3.jpg)
Havre de Grace's picturesque setting spoils tourists with romantic views of the Chesapeake Bay and the Susquehanna River. This delightful community of Harford County mixes history, culture, and nature to entice travelers from across the state. It conserves its seafaring heritage at the Havre de Grace Maritime Museum through an array of archives and relics collected over the years. Nature lovers and sightseers relish casual walks along the Havre de Grace Promenade to soak up stunning views of the water and the iconic Friends Concord Point Lighthouse. The rustic landmark has been a local mainstay since its installation in 1827.
![Havre De Grace city illuminated by the golden light of dusk.](/r/w768/upload/5b/e2/d3/shutterstock-2376478539.jpg)
Those who appreciate genuine human interactions should try shopping at the Havre de Grace Farmers Market. This a prime opportunity to meet friendly local vendors in a welcoming atmosphere and support their ventures.
Ocean City
![Aerial view of Ocean City in Maryland.](/r/w768/upload/18/91/eb/shutterstock-2361075313.jpg)
Ocean City is a top beachside getaway on the Atlantic Coast, where you can enjoy a relaxed vacation on pristine stretches of sand without worrying about choking crowds. At Ocean City Beach, locals and guests alike converge to lounge on the smooth sands and enjoy the water views. The beach sits right next to the Ocean City Boardwalk, where a string of eateries, souvenir shops, street performers, and other businesses create a socially inviting atmosphere to make new friends through amicable interactions.
![Wide aerial shot of Ocean City, Maryland, looking north at sunrise.](/r/w768/upload/76/20/da/ocean-city-maryland-aerial.jpg)
If you are interested in some little local history, pass by the Ocean City Life-Saving Museum and browse engaging exhibits chronicling life-saving on the Eastern Shore going as far back as the late 19th century.
The Old Line State is a one-of-a-kind destination on the East Coast, and these beautiful small towns in Maryland provide travelers with all the reasons to vacation there. Whether a historian, culinary enthusiast, or culture connoisseur, there is always something in the United States to guarantee a remarkable time. Each destination has a distinct personality and offers a novel experience to ensure a gratifying experience, from riding a scenic railway between the mountains of Cumberland to savoring sumptuous crab dishes in the quaint eateries of St. Michaels.