8 Picturesque Small Towns in Maryland for a Weekend Retreat
Feel merry and magical in the land of Maryland, where the national anthem of the United States, The Star-Spangled Banner, was written during the War of 1812. People have called this patriotic state “America in Miniature” since it contains every natural and geographic feature that defines America, except the desert. The many picturesque small towns in Maryland are excellent locales for a weekend retreat, especially if you want to venture out of the inconveniences of Baltimore or other big cities. From the shores surrounding the Chesapeake Bay to the mountains of the Allegheny, there are a number of photo-worthy towns for you to enjoy and for your cameras to capture. To see the beauty in the land of the free and the home of the brave, and experience what Maryland’s picturesque small towns have to offer for your weekend retreat.
Saint Michaels
Like the archangel Michael who defends good and righteousness, the town of Saint Michaels was “the town that fooled the British” during the War of 1812. St. Michael was essential for shipbuilding and trading since the 1630s, and fast sailing ships later called Baltimore Clippers were produced in the town to repel British ships in Chesapeake Bay. When British cannons fired on St. Michael, the townsfolk duped the British into thinking they were defeated by dimming their hanging lanterns and other lights. Today, the Cannonball House stands as one of the only surviving structures to have been shot. The Chesapeake Bay Maritime Museum and Store and St. Michaels Museum provide deeper insights into the pivotal Battle of St. Michael.
Aside from warfare, St. Michaels provides several fishing and boating opportunities through the Miles River and Chesapeake Bay. Scenic vineyards line the expansive Chesapeake Bay Wine Trail, while birdwatching is an awesome activity in the Blackwater National Wildlife Refuge. Last but not least, several lodgings such as Inn at Perry Cabin, St. Michaels Harbour Inn Marina & Spa, and St. Michaels Inn are a few of many opulent locations for you to gaze at the Miles River.
Hancock
Not John Hancock, but Edward Joseph Hancock, Jr—a Maryland hero who fight beside George Washington in the American Revolution—inspired the name for this simple town on the Potomac River. Sandwiched in the narrow path between Pennsylvania in the north and West Virginia in the south, Hancock has functioned as a vital crossroads between various locations between three different states. Both the C&O (Chesapeake and Ohio) Canal Towpath and the Western Maryland Rail Trail are the main attractions of Hancock, each pathway leading to unique and surprising destinations. One of these terminal points is the colonial-era Fort Fredrick State Park, an unassailable fortress that defended against attacks from Native American war parties and French legions. Nearby, the Green Ridge State Forest showcases majestic spectacles of the Appalachian ridges. For accommodations, look to the Hancock Motel for the services you require.
Thurmont
About 55 miles east Hancock, the thrilling town of Thurmont is a utopian dream made real for nature-lovers and adventurers. The Catoctin Wildlife Preserve and Zoo contains a menagerie of unique and amazing wildlife for your photos to memorialize. In addition, the Cunningham Falls State Park and Catoctin Mountain Park are perfect, picturesque locations for you to capture unblemished memories of the region. The Cat Rock & Bobs Hill Natural Area, in particular, promotes a stellar vantage over the landscape. Within these natural parks is the historic Catoctin Furnace, constructed in 1774 to manufacture ammunition during the American Revolution. One can also stumble upon the infamous Blue Blazes Still, a moonshine distillery from 1929 that has strange stories to tell.
Leonardtown
Approximately 60 miles away from Washington D.C., visitors can be entreated to the quaint community of Leonardtown. As home to the St. Mary’s Art Council, Leonardtown’s streets are brimming with a colorful Arts & Entertainment district replete with vibrant aesthetic displays and exhibits. With its location on the Potomac River, you can experience the joys of kayaking on the Leonard Wharf Park.
Let your curiosity guide you to the Amish and Mennonite communities of the area, particularly during November when the Amish Quilt Auction commences. Stroll through Leonardtown’s Butterfly Trail or Wine Trail for some fluttering or bubbling delights, respectively. Perhaps you might be intrigued to see the Molly Dyer Rock, said to hold the fading handprint of a local healer named Molly Dyer. Most people leave gifts to the late Molly Dyer on her rock, while all wisely do not touch it lest her ghost curses you. Whatever the case, do enjoy your time in Leonardtown.
Berlin
People who visit the small town of Berlin—just eight miles away from Ocean City and Assateague Island—is heavily influenced with the German culture or has something to do with the city of Berlin in Germany. But Maryland’s “Coolest Town in America” has zero connections to Germany’s capital city. In fact, it is widely believed that the town’s name a contraction of “Burleigh Inn,” a tavern at the crossroads of the Philadelphia Post and Sinepuxent Roads.
Regardless of this misunderstanding, Berlin is still a wonderful town full of history and culture. About 47 buildings have all been marked in the National Register of Historic Places, the Calvin B. Taylor Museum being the most prominent with historic artifacts and exhibits of Berlin’s past. The Mermaid Museum is also an interesting center for those who wish to know about strange mermaid sightings near Berlin. On July 7, do not miss Berlin’s annual Bathtub Races, a wacky and wild sport across several streets. Most importantly, do book a room at the historic Atlantic Hotel.
Crisfield
Overlooking the magnificent Tangier Sound and the lonesome Smith Island, the seaport town of Crisfield is famous for its nation-favorite seafoods like oysters, Maryland’s renowned blue crabs, and Chesapeake bivalves. Being called the “Crab Capital of the World,” one can charter boat trips and panoramic explorations in the southernmost edge of Chesapeake Bay, allowing opportunities to take pictures of the numerous fishing boats and crab-gathering crews do their duties to the community. The J. Millard Tawes Historical Museum illustrates Crisfield’s maritime legacy, while the Ward Brothers Workshop explores the transformation of pragmatic realism into expressive realization through decoy carvings. Lest you forget, find excellent lodgings at the Captain Tyler Motel or Rodeway Inn at Somers Cove Marina.
Havre de Grace
Havre de Grace (French for “Harbor of Grace”) is an opulent seaside settlement located at the mouth of the Susquehanna River and at the head of Chesapeake Bay. The small town was actually named after the port city of Le Havre de Grâce in France, and has continued to capture the soul of the Chesapeake through waterfowl decoys and carvings best seen at the Havre de Grace Decoy Museum. On the shores of Havre de Grace, with a splendid view of the vast waters and the Susquehanna National Wildlife Refuge, the towering Concord Point Lighthouse stands sentinel over the harbor, with the nearby Keeper’s House Museum elaborating on the oldest publicly accessible lighthouse in Chesapeake Bay.
Elsewhere, the Steppingstone Farm Museum exhibits rural crafts and arts depicting community life in the 1880- 1920 period. The Susquehanna Museum at the Lock House tell of Havre de Grace’s role in transportation, while the Lafayette Trail offers an interactive and immersive tour through history. There are many more excellent locations to visit in the “Decoy Capital of the World,” but the first places you should definitely consider are fine establishments like Vandiver Inn, the Spencer-Silver Mansion, and the White House.
Cumberland
Cumberland sits comfortably in a bowl-shaped valley bounded by the Potomac River. Only about 30 miles away west of Hancock, the town is a gateway to the Cumberland Narrows, a natural threshold carved by Wills and leading all the way to the majestic Allegheny Mountains. Although an unassuming settlement at first glance, George Washington once headquartered at a one-room cabin in Riverside Park, and was stationed at Fort Cumberland (for which the town is so named) in 1786 during the French and Indian War.
Visitors can enrich themselves to Cumberland’s dramatic transitions and transformations through several museums or learning centers, such as the Canal Place Heritage Area, the Allegheny Museum, and the National Civil War Museum. If you wish to brave the challenging heights of the Allegheny Mountains, then take a trip through the Great Allegheny Passage or along the Western Maryland’s Scenic Railroad (part of the C&O Canal Towpath). But if you wish to stay a while in Cumberland, look to Cumberland Inn & Spa for relaxation and leisure.
In Conclusion
Aside from “America in Miniature,” Maryland has been referred to as the “Old Line State” because revolutionary soldiers under George Washington held the line at the Battle of Bunker Hill and gained victory in Yorktown. But Maryland is also the “Free State” because its people fought and earned their independence. Now you can appreciate what Maryland’s ancestors did for the development of the US in the picturesque small towns you can visit in your weekend retreats. Whether you are admiring the decoy carvings of Crisfield and Havre de Grace, sightseeing Chesapeake Bay from St. Michael, or appreciating the cultures of Berlin and Cumberland, the star-spangled banner will hail you on your journey by the dawn’s early light.
