6 Eclectic Small Towns In Maryland

Maryland, the Eastern Seaboard state, was among the initial Thirteen Colonies and the seventh to achieve statehood in the Union. From cultural nuances in Bel Air and Berlin to the "Crown of the Chesapeake Bay," each eccentric town contributes a certain quality to this eye-catching Mid-Atlantic state.

Home to meandering rivers, islands, and mountains along the largest estuary in the world, its sobriquet is "America in Miniature." No wonder small towns get lost—a breeding ground for eccentricity. So collect your worn-out winter socks and greet spring in the capital, or plan a riverfront wedding next year in Elkton, the 20th-century Marriage Capital.

Annapolis

The capital of Maryland is one of the nation's smallest and most beautiful capital cities. Established in 1649 on the Severn River and Chesapeake Bay, the capital since 1694 beats with the heart of a small town, home to under 45,000. Painting its heritage along the walkable bayfront, discover Annapolis' captivating attractions on a morning jog with your dog, a historic walking tour, plus a delicious foodie heaven, particularly oysters. In between, you can spot notable buildings and cultural sites like the 1779 Maryland State House. From Armel-Leftwich Visitor Center, stop by the Romanesque St. Anne’s Episcopal Church with Tiffany glass windows and a historic cemetery.

Down the hill through the Historic District, to the waterfront, drop by the Maritime Museum and Park in the beautiful views of the Chesapeake Bay, cleaned and reinstated as a tourist destination. A boat tour reveals the stunning seaside profile. Truxton Park features a boat launch and a rec center, while Pirate Adventures delight kids of all ages. For almost half a century, the Annapolis Oyster Roast & Sock Burning has traditionally taken place on March 21st. Burning old winter socks at the communal roast welcomes spring with barefoot family fun, live music, and seafood. The United States Naval Academy houses monuments and the naval history in Beaux-Arts architecture since 1850.

Bel Air

Among its many hidden gems, Bel Air is a perpetual MD favorite. 40 miles northeast of Baltimore, this charming town with German heritage in the picturesque surroundings of Harford County features a living history book downtown. Housing shops, restaurants, and amusements for all ages, Bel Air Armory is a castle. Take in the small-town appeal of a tight-knit community along the tree-lined neighborhoods through scenic parks, welcoming amenities, and cultural events. Catering to both relaxation and socializing, nooks like Cozy Cookies or Looney's Pub offer moments of intimacy. “The Heart of Harford County” is under 30 minutes from the Bush River and the bay.

With access to the larger city, Bel Air is a perfect base for out-of-state visitors to relax at Bynum Run Park, take the Ma & Pa Heritage Trail, and let the kids play at Shamrock Park. Home to a number of amusement centers, like Jurassic Golf and Arcade, the 51-acre Rockfield Park features sports facilities, a large playground, nature trails, and a historic residence for events. Admire Liriodendron Mansion and seek natural serenity south at Harford Glen Park. At dinnertime, ranging from traditional southern cuisine to world foods, Vagabond Sandwich Company and Das Bierhalle Bel Air are next to Harford Artists Gallery to pick up original art or a special gift.

Berlin

Some 15 minutes inland from Ocean City, this German-settled town, named “America’s Coolest Small Town” 10 years ago, is more vibrant downtown than ever. Discover its unique cultural heritage with unique events and artistic flair. Filled with art galleries, boutique shops, and beloved eateries, don't miss the Blacksmith Bar & Restaurant at dinnertime in the historic district next to the Mermain Museum. Berlin, the filming location for the iconic films Runaway Bride and Tuck Everlasting, attracts couples and movie buffs from around the country. From the lively downtown, enjoy summertime recreation by Wachusett Reservoir, like an ink stain just northwest.

Just south of the state border, Berlin is at the doorstep of nature. Many enjoy the clear water views along Gates Pond Reservoir Loop Trail. Summer Star Wildlife Sanctuary is a beautiful area for a hike next to Barnes Hill Gardens, while the nearby Train Tunnel is a historic landmark. Whether you're in for the fall foliage, a summertime trek to Mt. Pisgah, or its North View, you'll begin to believe in the common prejudice that Germans like a good hike. Or, it is just a really pretty area, like Brewer Brook Dam Trail. North in Clinton, the Icon Museum and Study Center showcases church doors, Eastern Christian art, and saints, plus a tea room.

Elkton

This borderline town with Delaware to the east is like a toupee on Elkton River. Revealing the state's unique history, Elkton was the “Marriage Capital” during the early 20th century. Couples got married here without waiting periods, traveling long distances just to legalize their union. Honoring the sweet tradition and its famed legacy, the historic Elkton Municipal Building was once the most popular wedding venue. Drop by the Historical Society of Cecil County and, in the evening, Elkton Music Hall for a performance. Home to town greens, historic residences, and event venues, the nature is never far away.

From Cow Pond Recreation Area to Marina Park, take a morning stroll through the recreational Meadow Park at the heart with a creek, walking trails, sports fields, and playgrounds. Capriotti's Sandwich Shop crafts signature subs, salads, and kids' meals. Grab something from Sonny’s Italian Market and Deli for a picnic and follow the Big Elk Creek through the heart south to the river, where Woodlands Camping Resort is a popular summertime base close to the waterfront pier. The Elk River teems with fish and opportunities for outdoor fun, like boating. If you choose a downtown stay, saunter down to unwind at UnWined on the Water.

Havre de Grace

Known as the true "Crown of the Chesapeake Bay," discover what is behind the moniker in the "Haven of Grace." Where the Chesapeake Bay meets the Susquehanna River lies a lot of eccentricity, namely Havre de Grace. This poetic bayfront town boasts a historic downtown with waterfront views, entertainment venues, and festivals. Among MD's most beautiful and eccentric, it harbors scenic trails, parks, museums, unique bed and breakfast inns, specialty boutiques, and antique shops. Drop by the Havre de Grace Maritime Museum, which has exhibits and artifacts on local commercial fishing and crabbing, is a mainstay. The riverfront Lock House Museum in an 1840s house reveals the importance of canals. Rest your eyes scenically next door at Frank J. Hutchins Memorial Park.

The charming riverfront downtown offers a truly authentic Chesapeake Bay experience, rich in history and watery vistas with a calendar full of events celebrating its culture alone. It is easy to feel at home instantly amid an impressive mix of small-town businesses, each with a personality, and easy access to nature, like the unique Colored School Museum and Cultural Center. South along the shore, Swan Harbor Farm is a must-visit for a summer day in a lush, juicy place by a pier and waterfront trails. Catch a play at STAR Centre at the heart and enjoy the sunset from Millard Tydings Memorial Park, home to the river and yacht basin, a pavilion, and the most unique playground. Across town, Bulle Rock Golf Course is a celebrated green for scenic tee time.

Princess Anne

Just inland from Deal Island on Tangier Sound, Princess Anne is poised on both shores of the Manokin River. Home to the University of Maryland Eastern Shore, take a campus stroll before dinnertime at the unambiguous favorite, Caesar Pizza Palace, serving pizza and unpretentious pasta dishes in a bright, informal dining room with pastoral murals. The lively school year is followed by quiet summers, where the residents enjoy easy access to nature. Pocomoke State Forest is a quick drive east for riverside recreation like fishing and camping, plus boat rentals and a swimming pool.

Often overlooked, this artsy riverside town is a great detour on a coastal road trip in any season, from forest hikes to the Ella Fitzgerald Performing Arts Center. Take in the elegant downtown district on a stroll along the preserved 18th- and 19th-century buildings, including the iconic Teackle Mansion, with tours and seasonal events. The annual Somerset County Fair celebrates and showcases local agriculture and crafts. It is under 30 minutes south of Crisfield, indulging at Linton's Seafood and surrounding nature reserves, like Janes Island State Park, with fishing, boating, and camping.

Recognized as a "Free State" in 1864, Maryland doesn't draw a line on eccentricity. Princess Anne, a college town, is poised between the Tangier Sound and a state forest. From its quintessential capital to Bel Air, there's plenty of European charm through its Germantowns.

The laid-back vibes and the great outdoors may offer some respite from the city in chains. Bel Air is just over 25 miles northeast of Baltimore. So, free up a weekend to feast on local crab by the bay, browse vintage antiques, and spend the night at a unique B&B inn on a summertime escape in Havre de Grace.