8 Maryland Towns That Locals Love

As the “America in Miniature,” with approximately 10,460 square miles of land and water packed into a small area, Maryland is a compact region where one can find numerous beautiful small towns that locals love. From the delicious crab festivals to try out in small towns like St. Michaels and Crisfield, to historic and artistic landmarks located in Berlin and Leonardtown, locals love these Maryland towns. The following towns embody the endearing and enjoyable nature of the Old Line State, which played a significant role in the American Revolutionary War, delighting history buffs. No matter what attracts you to this region, you are sure to enjoy these small towns as much as the townsfolk do.

Saint Michaels

As one of the most vital and vibrant port towns on the Miles River, Saint Michaels attracts a variety of newcomers and travelers from all over due to its historic appeal and amenities. At the Chesapeake Bay Maritime Museum, you can learn more about the pivotal stories of the Chesapeake Bay and the lore of the people who contributed to the growth of Saint Michaels, complete with exhibits and active boat rides for you to tour significant points of interest. In contrast, the Classic Motor Museum of St. Michaels features more terrestrial vessels as one will find vintage vehicles ranging from antique farm tractors to classic automobiles. Some of you might also be interested in watching or attending the annual CBMM Waterman’s Appreciation Day & Crab Feast on August, which honors the individuals who make their living on the Chesapeake Bay with steamed crab and a boat docking contest. Whether you wish to learn more of the alluring past or soak in the spray and sunshine of the present, Saint Michaels is a saintly little town that locals love.

Frostburg

Home to the prestigious Frostburg State University, the lovable town of Frostburg beckons newcomers to discover beautiful landscapes and landmarks just eight miles away from the city of Cumberland. Because of its location at the head of the Georges Creek Valley, you can go adventuring in a handful of panoramic areas like the Dans Mountain Wildlife Management Area. Additionally, you can avail the assistance of the Tracks and Yaks, a bicycle rental service that offers railbike tours across the scenic Western Maryland Railway. At the Thrasher Carriage Museum, visitors can marvel at rare and extensive galleries of horse-drawn vehicles from the 1800s and early 1900s. Best of all, as Christmas draws near, Frostburg celebrates the holidays with the annual Storybook Holiday festival on December 6, when the downtown is packed with vendors, shops, and restaurants full of holiday specialties. With its cozy amenities and its attractive culture and neighborhoods, travelers visiting Frostburg will have a fun and fulfilling experience in this lovely little town.

Thurmont

Thurmont, a beloved small town just 20 minutes north of Frederick, invites newcomers to its laidback and leisurely community where the outdoors teems with townsfolks out on daily strolls. The Catoctin Mountain Park is a revered reserve with around 25 miles of trails and treks in a forested landscape, filled with idyllic camping sites and opportunities for fly-fishing at several waterways. Meanwhile, the neighboring Cunningham Falls State Park contains the Hunting Creek Lake to lounge about as well as a handful of waterfalls to photograph. Curious travelers might be eager to see the Catoctin Furnace, which was constructed in 1774 and provided ammunition for the American Revolutionary War for this small corner of Maryland. Finally, you can engage in serene horse-drawn carriage rides through the snowy streets of Thurmont on either December 6 or 12. One will not be overwhelmed by the small and simplistic landmarks to visit in the beautiful small town of Thurmont.

Emmitsburg

Near the state border separating Maryland from Pennsylvania, the pleasant small town of Emmitsburg prospers with its community events and its casual locations to seek out. Among the various festivities to wait for in Emmitsburg is the annual Turkey Trot, held in the month of November and celebrating Thanksgiving in a unique and compelling manner. Emmitsburg also celebrates its own version of Heritage Day with a frisbee/golf tournament, bike rides and bike rodeo, horseshoe contests, traditional field games, and live music for friends and family alike. Because the town itself is a well-preserved historic landmark boasting several historic edifices and landmarks to appreciate, you can start your self-tour of the area at the Frederick County Fire Rescue Museum with its exhibits and mementos of the firefighting past. Afterwards, you can venture out south towards the National Shrine Grotto of ​Our Lady of Lourdes, a sacrosanct Catholic landmark for curious outsiders and devout townsfolks to congregate towards. Having strong community ties and heritage, Emmitsburg emits a humbling and amicable atmosphere for newcomers to fall in love with just as the locals have.

Leonardtown

On the north shore of Breton Bay, the splendid town of Leonardtown is a prosperous homestead just a few miles south of Washington D.C. With access to the Potomac River, travelers and townsfolk alike can have some fun under the sun at vibrant beaches and landscapes as seen in the Newtowne Neck State Park. When it comes to aesthetics, the town’s Arts and Entertainment District is popular for its galleries, studios, shops, and even restaurants that satisfy the aptitudes and affinities of artists all over. Best of all, the town comes alive with music and festivities during the annual Leonardtown Summer Music Festival from April to October, where one can watch free outdoor performances and concerts the town square, known locally as the Wharf. Where visitors can soak in the beautiful waters of the Potomac River just a few miles away from the US capital, Leonardtown is a convenient and cozy destination to seek out.

Berlin

Just about 18 minutes west of Ocean City, visitors ought to explore the benevolent small town of Berlin. Coincidentally named after the capital city of Germany—though its true origins derive from “Burleigh Inn,” a tavern at the crossroads of the Philadelphia Post and Sinepuxent Roads—Berlin is a quirky destination as it hosts the whimsical Bathtub Race every July 7, where contestants ride on makeshift and renovated tubs down the streets. Equally as weird is the Mermaid Museum, which contains supposed artifacts belonging to mermaids spotted in the surrounding and nearby waters of Berlin. Additionally, you can take a self-guided tour through the Historic Downtown with its 47 individual structures that have retained their Federal, Victorian, and 20th Century formats. With as much culture and flair as its coincidental counterpart in Germany, the beloved Maryland town of Berlin enchants newcomers with gravitas and gallantry.

Crisfield

Lauded as the “Crab Capital of the World,” Crisfield enamors newcomers with its crustacean attractions and other notable landmarks to adore on Chesapeake Bay. One can suckle and sample on juicy crabs and lobsters while touring Crisfield's Arts and Entertainment District with the Corbin Studio & Gallery, artistically sublime destinations for you to fall in love with the culture and aesthetics of the town. Meanwhile, you can gallivant about to the north in the salt marshes and verdant trails of the Janes Island State Park. Those of you eager to go on boating trips can venture west towards Smith Island, a plentiful and biodiverse region with scenic landscapes in the Martin National Wildlife Refuge. Most importantly, you ought to attend the National Hard Crab Derby, a favorite annual Labor Day weekend event where townsfolks and even newcomers can engage in crab races, crab cooking, and other crustacean-themed activities to enjoy. Where seafood is fresh and merriment is in abundance, Crisfield is a wondrous gateway to the beauties of the Chesapeake Bay.

Oakland

Explorers and trailblazers enthusiastic for the laidback outdoors of Maryland’s Allegheny Highlands can travel close to the border line of West Virginia towards the amazing town of Oakland. The town serves as an energizing jump-off point towards Deep Creek Lake, the largest artificial lake in Maryland, where visitors can admire human ingenuity amidst natural appeal at the Deep Creek Lake State Park. Within the town’s confines, the Oakland B & O Railroad Museum chronicles the immersive and inspiring history of the rail and train system that allowed Oakland to prosper in the Allegheny Highlands. Of all the seasons of the year, autumn is the most revered, and Oakland celebrates fall with the annual Autumn Glory Festival where the townsfolk and travelers partake in parades and other activities for five days as the leaves turn red. Oakland’s quaint and laidback airs, paired with its proximity a manmade wonder, makes it one of the most loved and admired towns in Maryland to visit.

These Lovable Towns in Maryland Should Not Be Missed

Maryland is home to some of the most beloved and gorgeous small towns to visit as the year draws to a close. Visitors will be amazed by the compelling communities, the engaging festivities, and the unique attractions and amenities to experience. Oakland’s autumnal wonders, Crisfield’s crustacean features, and Thurmont’s natural landmarks are just some of the myriad of marvels that locals have loved for ages. Whether you are boating across Chesapeake Bay or adventuring through the forested regions around these lovable small towns, Maryland will treat newcomers with respect and aplomb that all will delight in.