9 Adorable Small Towns in Maryland to Visit in 2024
Embark on a nationalistic expedition to 2024’s most adorable small towns in Maryland. At the birthplace of "The Star-Spangled Banner," which rallied American troops towards freedom, you can take a break from the big cities like Baltimore and find relaxation and comfort from the heights of the Allegheny Mountains to the waters of the Chesapeake Bay. Explore the former homes and battlefields of American Revolutionary War heroes such as Saint Michael and Cumberland. Feel a sense of catharsis and awe in Hancock and Thurmont, where Maryland’s vast and untamed wilderness thrives. And get acquainted with the enthralling history and communities in Chesapeake City and Leonardtown. This year, follow the United States national anthem towards the most adorable small towns in Maryland.
Thurmont
Seek an idyllic destination for your vacation in the sublime abodes of Thurmont, a town only 50 miles from Hancock. Home to the Catoctin Wildlife Preserve and Zoo, there is a menagerie of majestic creatures to improve your awareness of animals everywhere. At the same time, the Cunningham Falls State Park and the Catoctin Mountain Park are magnificent regions that are sure to make you fall in love with nature’s splendors. Get an unspoiled and appealing vantage of Thurmont and its bucolic landscapes from atop the Cat Rock & Bobs Hill Natural Area.
Afterward, visit the historic Catoctin Furnace, built in 1774 to produce ammunition during the American Revolutionary War. You should also visit the Blue Blazes Still, an infamous moonshine distillery from 1929. Thurmont has many other adorable attractions and features for you to savor, so be sure to get your trekking gear and other apparel ready for a long trip in this simple, small town.
Hancock
Hancock did not earn its name from John Hancock—the first signer of the Declaration of Independence—but an American Revolutionary War soldier named Edward Joseph Hancock Junior who also fought for George Washington. You can find this humble community along the banks of the Potomac River in a narrow corridor between Pennsylvania in the north and West Virginia in the south. For generations, Hancock has been a waystation for travelers visiting from three different states, thanks to the C&O (Chesapeake and Ohio) Canal Towpath and the Western Maryland Rail Trail.
The colonial-era Fort Frederick State Park is a befitting example of Hancock’s geographic significance, as this formidable fortress withstood many foreign armies like those from France and also against Native American war parties. The Green Ridge State Forest will take travelers to the beautiful Appalachian Mountain Ranges. And splendid lodgings like the Hancock Motel will give you a blessed reprieve and rest in the serene air of Hancock.
Leonardtown
Approximately 60 miles away from the capital city of Washington DC, Leonardtown lounges on the Potomac River and offers innumerable enterprises and entertainment for everyone. One can relish in the adorable artistry and superb culture of Maryland at St. Mary’s Art Council, home to a cornucopia of aesthetic masterpieces in the Arts & Entertainment district.
The Amish and Mennonite communities in Leonardtown entreat everyone to the Amish Quilt Auction in November. Walk through Leonard Wharf Park or follow the Butterfly Trail or Wine Trail. There is also the town’s greatest curiosity, the Molly Dyer Rock. Legends say that the fading handprint on the rock belonged to a local healer named Molly Dyer, and one should not touch or disturb the lest you incur Molly Dyer’s ire.
Saint Michaels
Saint Michaels is a thriving trading and fishing port by the waters of Chesapeake Bay. At the Miles River and Chesapeake Bay, one can go fishing for some of the freshest and rarest bounties in Maryland. One might also be interested in the Chesapeake Bay Wine Trail, flanked by dozens of lavish vineyards. Birdwatchers should explore the Blackwater National Wildlife Refuge. History lovers will appreciate visiting the Chesapeake Bay Maritime Museum and Store, the St. Michaels Museum, and the Cannonball House, the latter being the only surviving structure that withstood British cannons during the War of 1812.
Saint Michaels happens to be “the town that fooled the British,” not only because of agile ships called the Baltimore Clippers that outmaneuvered slower British frigates in Chesapeake Bay, but also because the townsfolk dimmed their hanging lanterns to trick the British into thinking they lost. So immerse yourself in a town as good-natured and righteous as the archangel Michael, and stay a while in fine accommodations such as the Inn at Perry Cabin, St. Michaels Harbour Inn Marina & Spa, or St. Michaels Inn.
Berlin
Despite not having any connection to the capital city of Germany, Berlin is still one of the best tourist destinations in Maryland. After all, it has been called one of the “Coolest Towns in America.” People from Ocean City and Assateague Island—both eight miles from Berlin—may want to rent a room at the Atlantic Hotel. One of many good reasons to stay a while in Berlin is the 47 buildings all belonging to the National Register of Historic Places.
The Calvin B. Taylor House Museum, for example, contains historic relics that contributed to the town’s inception. There is also the Mermaid Museum, which showcases sightings and rumors of mermaids in Berlin. Most importantly, on July 7, the annual Bathtub Races will see people charging down the main thoroughfares on makeshift vehicles—mostly bathtubs on wheels. So enjoy the adorable and wacky marvels of the Coolest Town in America.
Crisfield
Crisfield is the type of town for people who need a bit of seafood in their diet. It is the “Crab Capital of the World,” and as such, one can sample Maryland’s nutritious and delicious Chesapeake bivalves, blue crabs, and oysters of all varieties and shapes. You can charter a fishing boat expedition in Tangier Sound and towards Smith Island, or you can dive into the past at the J Millard Tawes Historical Museum.
The more creative and industrious of you might fancy the Ward Brothers Workshop, where some of the best decoy carvings in the state can be perused and even purchased. There is no shortage of cute and delightful attractions in Crisfield, especially in accommodating hostels such as the Captain Tyler Motel and Rodeway Inn at Somers Cove Marina.
Havre de Grace
Havre de Grace means “Harbor of Grace” in French, and the town itself was named after the port city of Le Havre de Grace in France. As a graceful harbor on the Susquehanna River that leads out into the Chesapeake Bay, Havre de Grace shines proudly as the “Decoy Capital of the World.” There, one can tour the Havre de Grace Decoy Museum to admire some of the best waterfowl and duck decoy carvings. There are also real ducks and other birds at the Susquehanna National Wildlife Refuge.
You might fancy seeing the whole harbor from atop the Concord Point Lighthouse. You can also visit the Keeper’s House Museum to learn about the oldest publicly accessible lighthouse in Chesapeake Bay. The Steppingstone Farm Museum exhibits an impressive collection of local crafts and masterpieces from 1880 to 1920. In contrast, the Susquehanna Museum at the Lock House informs people about the Lafayette Trail, which contributed much to Havre de Grace’s growth. Those of you intrigued by the amiable wonders of Havre de Grace can feel more grateful and graced by the fine lodgings of the Vandiver Inn, the Spencer-Silver Mansion, or the White House.
Cumberland
About 30 miles from Hancock lies the adorable small town of Cumberland. With its location in the Cumberland Narrows—a bowl-shaped valley that the Allegheny Mountains surround—and tangent to the Potomac River, Cumberland is an idyllic spot for rest and recuperation. Indeed, George Washington headquartered in Cumberland during the Revolutionary War, and rested in a one-room cabin in Riverside Park. Fort Cumberland stands as a proud monument to victory when, in 1776, during the French and Indian War, it withstood many a siege and skirmish against invading forces.
To learn more about Cumberland’s revolutionary past, you can head over to the Allegany Museum and Canal Place Heritage Area. The Western Maryland’s Scenic Railroad—part of the C&O Canal Towpath—and the Great Allegheny Passage are scenic routes you can traverse to see more of the Allegheny Mountains. No need to worry about accommodations, because the Cumberland Inn & Spa will have you feeling at home in Cumberland.
Chesapeake City
When Bohemian map maker Augustine Herman came upon a soon-to-be commercial canal called Back Creek that trickles out into Elk River, he decided to erect the Village of Bohemia—or Bohemia Manor—in the early 17th century to connect Chesapeake Bay with the Delaware River. Today, the Village of Bohemia is now known as the small town of Chesapeake City. The C & D Canal Museum illustrates the effort to widen the canal that connects the Chesapeake Bay with the Delaware River, and in the south, you will find the historical edifices of Saint Francis Xavier Church and Worsell Manor.
Although it is one of the smallest towns in Maryland—with a population of less than 800 people—you can still find small moments of enjoyment in this adorable small town. Only an hour away from Baltimore and Philadelphia in Pennsylvania, let the cute rooms of the Blue Max Inn entreat you to a lovely stay in Chesapeake City.
Maryland is a state that has affected and was affected by many moments in history. As the “Old Line State,” George Washington's armies held the line at the Battle of Bunker Hill and conquered Yorktown. As the “Free State,” Maryland’s people were the fiercest to gain independence from the British Empire, the French Empire, the Spanish Empire, and other powers from Europe. But most of all, as “America in Miniature,” nearly every geographic landscape in America—except the desert—can be seen in Maryland.
Of course, Maryland is most renowned for its most adorable small towns, and one can observe the three different titles of Maryland manifested in these cute villages like Cumberland, Chesapeake City, Crisfield, and more. So use what freedom and time you have to explore 2024’s most adorable small towns in Maryland.
