8 Most Quaint Small Towns in Maryland
Having beautiful sprawling coastlines along the Atlantic Ocean and Chesapeake Bay, Maryland is a spectacular Mid-Atlantic state, bordered by the District of Columbia and the US states of Delaware, Pennsylvania, West Virginia, and Virginia. Being one of the initial Thirteen Colonies, Maryland is sprinkled with countless towns and cities that are great destinations for delving into colonial history in quaint settings. Besides touring the state’s urban metropolises like Annapolis, Baltimore, Columbia, and Germantown, spare some time to visit the adorable small towns dotting this Old Line State.
Berlin
Crowned “America’s Coolest Small Town,” this tiny Worcester County town named after the old tavern “Burley Inn” is located just 10 miles inland from Ocean City and Assateague Island National Seashore. A part of the Salisbury, MD-DE Metropolitan Statistical Area, Berlin is best known for its revitalized historic downtown commercial district and adjoining residential areas that feature several meticulously maintained late-19th-century landmark properties in different architectural styles lining the scenic tree-lined streets. History buffs must visit the Atlantic Hotel, Burley Manor, Henry’s Grove, Rackliffe House, Merry Sherwood Plantation House, Calvin B. Taylor House Museum, and the mind-blowing Mermaid Museum. Outdoor enthusiasts are attracted to the idyllic natural landscape of the Assateague State Park, which has the distinction of being Maryland’s sole oceanfront park. Downtown Berlin is also home to shops, art galleries, and notable eateries like Blacksmith, The Globe, Boxcar on Main, Rayne’s Reef Soda Fountain & Grill, and the Burley Oak Brewing Company. Throughout the year, the town hosts many events, such as the Berlin Farmers Market, 2nd Friday Art Stroll, Berlin Spring Cruisers Classic Car Show, Berlin Bathtub Races, Peach Festival, Oktoberfest, and Berlin Christmas Parade.
Bel Air
Harford County’s seat, Bel Air, is a laid-back town in Northeast Maryland about 30 miles north of downtown Baltimore. Planned on a portion called “Scott’s Old Fields” of an inherited land by Aquilla Scott, Bel Air, and its neighboring suburbs have grown substantially over the years, transforming the town into the county’s governmental, cultural, commercial, educational, and medical center. Hike along the Ma and Pa Trail and explore some of Bel Air’s must-visit attractions like the Bel Air Armory, Liriodendron Mansion, Tudor Hall, the Hays House Museum, Priest Neal’s Mass House & Mill Site, Thomas Run Church, Hartford Mall, etc. Many of Bel Air’s downtown is part of the Bel Air Arts and Entertainment District – one of the state’s 29 designated arts and entertainment districts, mainly used for concerts, art galleries, theaters, dance performances, festivals, and other annual cultural events. The town also maintains one community park (Rockfield Park) and five neighborhood parks, offering various recreation amenities such as play equipment, extensive trails, horticultural gardens, picnic facilities, and an amphitheater supporting an active summer concert series.
Chesapeake City
This Cecil County town, originally called “the Village of Bohemia” by the famous Bohemian surveyor Augustine Herman, was rechristened in 1839 after constructing the Chesapeake and Delaware Canal (C&D Canal). Divided into northern and southern sections following the canal’s construction, Chesapeake City is the only town in the state to be placed on a working commercial canal. Most of the town’s fascinating 19th-century architecture is found on the canal’s southern shores, and many of these structures house picturesque vintage stores, art galleries, boutiques, outstanding bed & breakfasts, and cozy diners like the Bayard House Restaurant. Chesapeake City’s other places of interest include the C&D Canal Museum, Chesapeake City Water Tours, M/V Bay Breeze, and the Chesapeake Inn Restaurant and Marina. Chesapeake City’s primarily residential northern section is well-known for the 17-mile-long Ben Cardin C&D Canal Recreational Trail and Schaefer’s Restaurant & Canal Bar.
Havre de Grace
A scenic hamlet in Maryland’s Harford County named after Le Havre, a French port city, Havre de Grace is located at the Susquehanna River’s mouth and the head of the expansive Chesapeake Bay, approximately 75 miles northeast of Washington, D.C. Havre de Grace’s strategic location makes it the most sought-after tourism and recreation destination that is celebrated for its stately Victorian homes, bayfront views, marinas, Havre de Grace Yacht Basin, Havre de Grace Promenade, and engrossing museums like the Havre de Grace Maritime Museum, Lock House Museum, Steppingstone Museum, Decoy Museum, and Concord Point Lighthouse. The two parks, Susquehanna State Park and Millard Tydings Memorial Park offer many family-friendly activities amidst breathtaking surroundings.
Mount Airy
Forming a portion of both the Washington Metropolitan Area and the Baltimore-Columbia-Towson Metropolitan Statistical Area, Mount Airy is placed on the boundary between Frederick and Carroll counties in Central Maryland, within 40 miles of two major cities: Washington D.C. and Baltimore. Initially settled along the Baltimore & Ohio Railroad line, the town’s name was suggested by an Irish B&O worker who, on a windy work day, complained about his freezing ears due to the cold winds that blew across Parr’s Ridge. The town’s Main Street is lined by historic buildings built using the Colonial-revival architectural style, besides countless boutique shops, galleries, cafes, casual restaurants, parks, farms like Gaver’s Farm and Knill’s Farm Market, and local wineries and breweries, including Elk Run Vineyards, Linganore Winecellars and Milkhouse Brewery at Stillpoint Farm.
New Market
Often referred to as the “Antiques capital of Maryland,” this Frederick County town was platted as a stopping point on U.S. Route 40 (Old National Road) between Baltimore and Frederick. The entire town forms a part of the New Market Historic District and is packed with many buildings that date back to the 19th century. Downtown New Market features numerous antique shops like Fleshman’s Antiques, Smith Tavern Antiques, RP Brady Antiques, etc., with their vast collection of antiques from bygone eras, besides other locally owned businesses and friendly dining venues such as The Vintage Restaurant and the Derby Restaurant & Bar. Every year, New Market hosts various events and festivals like the periodic 2nd Saturday events (from June to October) and “Christmas in New Market” on the first Saturday of December.
Saint Michaels
Billing itself “The Heart & Soul of the Chesapeake Bay,” Saint Michaels is an attractive harbor town in Talbot County along the Miles River. This quintessential Eastern Shore getaway proudly upholds its moniker “the town that fooled the British,” with its walkable downtown boasting Victorian mansions currently housing local stores, stylish boutiques, and excellent bed & breakfasts. Some of the town’s engaging attractions include the Saint Michaels Mill, Chesapeake Bay Maritime Museum, St. Michael’s Museum, 1879 Hooper Strait Lighthouse, Classic Motor Museum, and different art galleries like Gregorio Gallery, Ouvert Gallery, A.M. Gravely Gallery, Hopkins Original Art, and Simply Dragonfly. For a typical Maryland gastronomic experience, head to The Crab Claw, Bistro St. Michaels, Ava’s Pizzeria & Wine Bar, Justine’s Ice Cream Parlor, Limoncello Italian Restaurant & Wine Bar.
St. Mary’s City
Established in 1634 and christened after the Virgin Mary, this historic town in Southern Maryland is located along the St. Mary’s River on the Chesapeake Bay’s western shores, about 15 miles southeast of Leonardtown. The state’s foremost European settlement and capital, St. Mary’s City, is an extensive state-run historic area home to a community of around 933 inhabitants. In addition to the principal campus of St. Mary’s College of Maryland, St. Mary’s City contains uncountable living history museums, reconstructed colonial buildings, and an outdoor archaeological park. One of the finest ways to experience authentic colonial life is by stepping onboard the Maryland Dove and taking informative tours. Also, do not forget to visit the St. John’s Site Museum, the Godiah Spray Tobacco Plantation, “The State House,” and the Woodland Indian Hamlet. After a hectic day of exploration, spend a relaxing night at The Inn at Broome Howard, considered Southern Maryland’s most historic bed & breakfast.
From the most incredible small town of Berlin to the rich colonial heritage of St. Mary’s City, the nation’s eighth-smallest and 18th-most populous state boasts a plethora of impressive small towns. Each postcard-pretty town attracts vacationers from all over the globe with incredible scenic splendor, panoramic coastal views, varied cultural heritage, delicious cuisines, and a welcoming ambiance. Whether you want to explore the historic sites or do some boutique shopping, these quaint small towns in Maryland are worthy places to visit for lifetime experiences.
