7 of the Most Charming Small Towns to Visit in Maryland
Bursting with charm and quaintness, the southeastern state of Maryland along the coast feels like everything you've been dreaming about after a long winter of work, errands, and other activities. Melt the stress away in Thurmont, an ambient small town in the foothills of the Catoctin Mountains with so many hikes to choose from.
As one of the original 13 colonies in the United States, the first town is a great introduction to the colonial history of the state, while the famous Captain John Smith explored the area around the last town back in 1608. For fresh local seafood, Crisfield offers Chesapeake's best from any of its shacks or fine dining venues.
Bel Air
Just 45 minutes north of Baltimore, Bel Air is a charming town along the East Coast with a name that breathes serenity. Once a stop along the underground railroad, it is widely recognized today for its historic district, which mixes distinct architecture like the must-see Liriodendron Mansion or Tudor Hall with shopping opportunities, including many local boutiques, great dining at delicious restaurants like the unmissable Bonefish Grill, as well as outdoor cafes to soak in the views and breweries to unwind in the evening. From explicit art galleries to adventurous parks, don't miss a tour of the Hays-Heighe House on the campus of Harford Community College, just a few miles out of the vibrant downtown.
Blissful nature is just a hand's reach away at Bynum Run Park with a pond, the spectacular boardwalk through the forest, the Ma & Pa Heritage Trail, or the extraordinary Heavenly Water Park adjacent to town. Whether you're in for outdoor recreation or are an enthusiast for art, literature, and architecture, there's a reputable stay for each group, including the family-friendly Country Inn & Suites by Radisson and the Hilton Garden Inn Bel Air. Discover the artsy side of Bel Air through Harford Artists Gallery, Emily Bayless Graham Park, and The Chesapeake Gallery.
Berlin
Revealing its rich heritage with a telling name, Berlin, just a quick drive from Ocean City is also "America's Coolest Small Town." Offering easy access to the iconic Assateague Island National Seashore, it's the perfect base for outdoor enthusiasts from the big city, home to friendly locals and beautiful streets of restored Victorian architecture, boutique shops, and gourmet restaurants. The offbeat Berlin Arts and Entertainment District is a must-see for every culture fan to browse and buy from local talent through over 60 shops, in between entertainment, galleries, and welcoming studios amidst a celebratory atmosphere in the accompaniment of live music and events.
The town dials up the charm every second Friday of the month during the art stroll with more live music and local displays that can be your unique gift for a friend or a home decor piece. Visitors enjoy a variety of outdoor activities, like summertime concerts in the park and, in the fall, the popular peach festival. Tucked into the countryside charm of eastern Maryland, just 10 miles from Ocean City, Berlin is a favorite getaway for antique shopping, delicious restaurants, and a historic atmosphere, with the Atlantic Hotel as its historic centerpiece from the late 19th century. Welcoming guests for a 3-star stay, it hosts the quirky yet beloved Berlin Fiddlers Convention with musicians and bluegrass fans over a weekend of live music.
Boonsboro
Boonsboro, a historic town from 1792 at the foot of South Mountain, is naturally bountiful and historically charming. Offering a quick escape right between Hagerstown and Frederick, let's start with the fact that Daniel Boone's cousins, George and William Boone, founded it at the rural crossroads town, now a getaway for regional heritage tourism, like colonial and Civil War heritage sites. From the National Road to Washington Monument State Park and Antietam National Battlefield, its own Town Museum features historical artifacts.
Under an hour and a half from Baltimore in Southern Washington County, Boonsboro is the state's classic book cover town, with scenic outdoors, historic sites, and charming bed and breakfasts, completing its picture book appeal. You can stay at the New York Times best-selling author Nora Roberts' own, the welcoming Inn BoonsBoro. This beautiful, historic B&B is right on the Square, so don't miss the 1902 Trolley Station, the C&O Canal Towpath, minutes from town into nature, and the proximity to the Appalachian Trail, which excites the adventurers.
Crisfield
Established as a fishing village along the Tangier Sound in the embrace of Chesapeake Bay, the locals call it the "Seafood Capital of the World." Otherwise known as the “Crab Capital of the World," they also insist that the downtown lies upon a foundation of crushed oyster shells. Regardless of what you go along with, this city, unlike any other, is, to this day, a hotbed for fishing and seafood fans. Crisfield charms every type of traveler with its historic ambiance, sea delicacies, and opportunity to reel in your own catch.
From fresh crab to lobsters, mussels, clams, and all kinds of fish, once you taste Chesapeake's best right here from any shack or fine dining venue, you will never go back home and order seafood from a ho-hum restaurant at home. Others know Crisfield as the place to create lasting memories outdoors, particularly the close wildlife encounters through the stunning Janes Island State Park. Home to welcoming residents, unique festivals, and remarkable sunsets that make you linger just another day longer, among other kept secrets of the state's Eastern Shore of Maryland, Crisfield makes every experience unforgettable.
Solomons
Located on the southwestern shores of Maryland’s Bay, Solomons Island is home to just over 2,000 residents who love living in this charming Chesapeake Harbor. Fun, friendly, and full of attractions, tangled amid the protected waters of the Patuxent River and Back Creek, this boater's paradise offers numerous anchorages, moorings, and marinas with transient docks. Don't miss Calvert Marine Museum, which highlights the best of the Maritimes over an impressive exhibit, aquarium, and boat restoration facility, with the original Drum Point Lighthouse, an 1883 wood and cast iron lighthouse at its centerpiece. Climb the entire light of this one of the four survivors from the Bay's original 42 up the narrow spiral staircase to the glorious Fresnel Light at the top. The little ones love nuzzling face-to-face with sharks, seahorses, lionfish, and the comic, playful sea otters, while the outdoor display of antique boats delights sailors of every age with the evolution of pleasure boating exhibits.
Solomons adapts to every taste of a getaway against relaxing scenery, like an easygoing downtown area, a good dozen waterfront restaurants, and a Tiki Bar for a feel of the tropics in the southern state. Board a Heritage Tour for a boat cruise through the harbor or get your own vessel along the Riverwalk with boat rental shops and ice cream parlors against the views. There's also art through Annmarie Sculpture Garden and Art Gallery that rivals its likes in Seattle and Boothbay Harbor with its surprising and serene artworks. The attractive waterfront community at the confluence of the rivers is also home to the Pavilion on Lord Baltimore Bay waterfront along the western shore of Solomons Island Road, with spanning views of the tremendous Governor James Johnson Bridge across the Patuxent Bridge to St. Mary’s.
Thurmont
Visitors love Thurmont for its feel of tranquility, where the stress starts melting away at the view of the ambient small townscape in the foothills of the Catoctin Mountains, a glorious place to stretch your legs over many hikes. An awe-inspiring getaway for outdoor enthusiasts and culture lovers, it is one of Maryland's best for jaw-dropping scenery, accessible all over the easy enough trails for kids to the winding ones through Catoctin Mountain Park. The easternmost section of the Blue Ridge Mountains, proximate to Cunningham Falls State Park, is popular among sightseers, wonder-seekers, and photographers to capture the beauty of the state's largest cascading waterfall from 78 feet.
Thurmont, in the heart of Maryland, is an idyllic base for some of the state's best wildlife spotting, rock climbing, fly-fishing, and even cross-country skiing. Get a fill of history at the Blue Blazes Whiskey Still exhibit, while Catoctin Mountain Park is home to Camp David, the presidential retreat. Tangled amid twenty-five miles of hiking trails, the well-marked trails for every level include the popular Cunningham Falls Trail, with camping, fishing, and swimming in the area during the summer. Don't miss the landmark Loy’s Station Covered Bridge, while the annual Catoctin Colorfest in October is one of the East Coast's largest outdoor craft shows.
Vienna
Vienna, a charming MD town in Dorchester County, is that one, one among the many in the easternmost part of the state, with a picture-perfect waterfront. Vienna makes up for its diminutive size with historical significance and an excited population of friendly locals. Bursting at the seams with charm and life, visitors can enjoy outdoor activities on the nearby Chicone Creek with views across the Nanticoke River Bridge, as well as regular local events like fishing tournaments.
Welcoming you to experience the pleasant riverside lifestyle along the Nanticoke River, the natural environment speaks for itself through the most popular Vienna Waterfront Park, a boating dock, and trails to soak up the views on a stroll or relax at sunset. Born after the famous Captain John Smith explored the area back in 1608, Vienna blends historic charm with rural beauty and local amenities, where each feat,ure complements the tiny town's quaintness, just southeast of the bustling Cambridge, like the unique Handsell House and the must-hit Millie's Road House Bar for the evening.
Maryland is home to many fantastic towns such as Berlin, the gateway to Assateague Island National Seashore, which is just a quick getaway from Ocean City for the offbeat Berlin Arts and Entertainment District. Visit the distinct Solomons, a charming Chesapeake Harbor town on the southwestern shores of Maryland’s Bay, tangled amid the protected waters of the Patuxent River and Back Creek—every water fan's dream! Boonsboro is also truly a mountain idyll, discovered by Daniel Boone's cousins, George and William Boone.
