11 Unforgettable Small Towns to Visit in Maryland
Despite its relatively small size, Maryland is one of the most geographically diverse states in the nation. Except for a desert, you can find almost every other type of landscape in its minute territory, from the Chesapeake Bay and the Blue Ridge Mountains to Green Ridge State Forest and the Susquehanna River. However, this is hardly all that makes Maryland special; the state is also renowned for hosting the oldest continuously used state capitol, its staple blue crab cuisine, and diverse cultures. In essence, it is a mixed bag of surprises that any traveler would be lucky to explore.
Whether a history lover, a nature enthusiast, a culinary connoisseur, or a culture vulture, there is something about the region's small towns that leaves a lasting impression on first-timers. From swimming with wild ponies in Berlin to reliving America's bloodiest day in Sharpsburg, here are unforgettable small towns to visit in Maryland.
Berlin
Berlin gets its "it factor" from the paradisiacal Assateague Island State Park, a unique barrier island on the Atlantic Ocean, renowned for its wild ponies. The reserve allows tourists to marvel at feral ponies roaming about casually, and take advantage of two miles of pristine ocean beaches to swim, sunbathe, beachcomb, fish, and surf against a picturesque backdrop. Berlin's historic downtown is unlike any other in small-town America, featuring an Arts and Entertainment corridor with an eclectic blend of over 60 restaurants, museums, galleries, coffee shops, and live music venues within elegant Victorian buildings. A magical experience awaits at the Mermaid Museum, where guests can see, touch, and hear everything mermaid from a curated collection of quirky photographs, sculptures, hair, scales, and other artifacts chronicling the history of the mythical creature.
The landmark neighborhood also hosts an array of colorful events and festivals, breathing life into the community. Arguably, the most memorable among them is the annual Bathtub Races. This high-octane, family-friendly event brings everyone together for a night of fun, with participants racing down the streets in bathtub-inspired vehicles, creating a one-of-a-kind spectacle.
Sharpsburg
This tiny town in Washington County has a unique mission to remind travelers of one of the bloodiest days in American war history. Serving as the epicenter of a highly contested Civil War battle in 1862, Sharpsburg hosts the Antietam National Battlefield, where 12 hours of exchanges between the Union and the Confederacy culminated in 23,000 casualties. Newcomers can get the area's map and embark on a self-guided auto tour to explore monuments like the historic Burnside Stone Bridge and experience the gravity of walking these hallowed grounds. The Kennedy Farm is another crucial portal to the nation's history. This dilapidated structure housed the famous abolitionist John Brown and his men in 1859 as they prepared to launch an attack on the Federal arsenal on the other side of the Potomac River in Harpers Ferry.
The fully restored farmhouse instills a strong feeling of nostalgia that places you in the shoes of Brown's men in the build-up to the raid. History aside, Sharpsburg welcomes visitors for a delicious tasting tour at Antietam Creek Vineyards. This delightful 55-acre wine crafting facility and tasting room specializes in estate-grown Bordeaux-style wines, offering a relaxed setting for enjoying a glass of wine while overlooking the Antietam National Battlefield.
Havre De Grace
A unique blend of waterfront charm, maritime heritage, and vibrant arts draws visitors to this Chesapeake Bay community. Havre de Grace boasts a picturesque setting, allowing first-timers to witness the dramatic overlap of the Susquehanna River and Chesapeake Bay waters from the Havre de Grace Promenade. This scenic boardwalk stretches about half a mile and provides a serene setting and an unprecedented vantage point for viewing the scenery and majestic bald eagles. The Havre de Grace Decoy Museum presents a truly special American cultural experience. It features an impressive collection of intricately carved waterfowl decoys as a tribute to a longstanding hunting tradition in the Chesapeake Bay region.
Havre de Grace's artistic side shines through the Cultural Center at the Opera House. This state-of-the-art hub hosts professional plays, theater performances, dance shows, live music, and other local events, demonstrating the community's devotion to the arts. Newcomers are often drawn to the sense of belonging and the rustic charm of the 1870 building.
Cumberland
Western Maryland looks irresistible when you view it from Cumberland, punctuated by spectacular Appalachian landscapes. Many travelers come to explore the scenery aboard the Western Maryland Scenic Railroad. This nostalgic train ride takes passengers on an excursion through the Cumberland Narrows, promising stunning vistas of the Appalachian Mountains and Willis Creek. The trips are creatively themed to reflect the seasons, ranging from the Murder Mystery Dinner Trail and the Polar Express Train Ride to the Allegheny Winter Express.
Cumberland boasts a well-preserved historic district, where a mix of 19th- and 20th-century architecture showcases its rich heritage. The Gordon-Roberts House invites guests to step back in time for a glimpse of the Victorian days. Built in 1867, the Second Empire building was the home of local attorney Josiah Hance Gordon and features costumed tour guides who lead guests through three floors of period exhibits and furnishings, depicting the lifestyle of a middle-class family at the time. Foodies will love sampling the delicious cuisine served within downtown Cumberland, especially at the landmark Baltimore Street Grill. For over 25 years, this local staple has been tantalizing palates with its combination of Cajun, American, and Italian dishes, served in a fun and lively atmosphere. Its dynamic menu features delicacies like Jambalaya, shrimp creole, crawfish, and yellow-fin tuna.
Crisfield
There is a special reason they call Crisfield the Seafood Capital of the World, and vacationers will notice this during the National Hard Crab Derby. Held annually over the Labor Day weekend, this crab-themed event celebrates the watermen's culture in the Chesapeake Bay region and the seafood heritage of the Eastern Shore through activities such as crab-picking contests, crab races, the Miss Crustacean pageant, and boat docking competitions. The surrounding Chesapeake Bay waters invite sightseeing cruises to the nearby islands courtesy of Experience Smith Island. This day-long excursion introduces guests to the pastoral beauty of Smith Island, while offering them a chance to interact with native islanders, speculate on soft shell crabs, and taste the trademark Smith Island Cake.
Finally, culture lovers can discover Crisfield's artistic heart by roaming through the Crisfield Arts and Entertainment District. This lively community of creatives provides a welcoming atmosphere for guests to be inspired by watching painters, woodworkers, sculptors, and live performers as they work through their creative process. It is also home to the Corbin Studio & Gallery, where they can admire and buy original pieces.
Ocean City
Ocean City is one of the most unforgettable small towns to visit in Maryland, thanks to its waterfront serenity, picturesque boardwalk, and pristine beaches, which create a classic beach resort vibe. The Ocean City Boardwalk is a central gathering spot for tourists, providing a 3-mile oceanfront where people come to stroll, cycle, jog, and people-watch. It is lined with dining and entertainment spots, as well as exciting attractions, highlighted by Jolly Roger Amusement, Ripley's Believe It or Not, and Fisher's Popcorn. The promenade offers direct access to the 10-mile Ocean City Beach, where silky-soft sands and pristine Atlantic Ocean views provide tourists with a serene environment in which to unwind.
The expansive beach serves as a platform for electrifying annual festivals, highlighted by the Oceans Calling Festival. This popular music and food festival attracts over 150,000 attendees and features three days of more than 40 musical performances by renowned headliners on three different stages. It is one of the most memorable beachside festivals in the state.
St. Michaels
St. Michaels boasts one of the most impressive maritime museums on the Eastern Shore. It is home to the Chesapeake Bay Maritime Museum, situated on an 18-acre waterfront campus featuring nearly a dozen buildings filled with authentic historical exhibits. These include a working boatyard, tugboats, the picture-perfect Hooper Strait Lighthouse, and one of the few remaining skipjacks in the region, ensuring a hands-on connection to the rich nautical history.
Downtown St. Michaels is a treasure trove of unmissable gems, such as the Classic Motor Museum. This fascinating facility offers a special tour of America's automotive heritage, showcasing a stunning collection of classic cars. Highlights include an International Harvester pickup truck from the early 1900s, a 1931 LaFrance fire truck, vintage motorcycles, and mid-century muscle cars. Outdoor enthusiasts can retreat to Muskrat Park, a half-acre waterfront oasis nestled amidst scenic and serene surroundings, to unwind. The park features a gazebo, picnic tables, walking paths, and terrific harbor views.
Smith Island
Smith Island is Maryland's only occupied offshore island and boasts an array of unique attributes, including a dying traditional waterman heritage, a distinctive dialect, and the state's official dessert. It takes an hour-long ferry ride to access Smith Island from Crisfield, giving it an isolated charm that few visitors explore. The village is famous for the Smith Island Cake, which newcomers can sample at Bayside Inn Restaurant. This pleasant diner makes for an excellent first stop, where tourists can order the multi-layered chocolate cake and enjoy sumptuous fresh-caught crab dishes.
Meanwhile, the Smith Island Cultural Center offers a special glimpse into the life of watermen on the island, their families, and their heritage. It screens a 15-minute documentary about the region and showcases artifacts that highlight tradition, crabbing, watercraft, and more.
Olney
Olney charms tourists with one of the most dazzling Christmas light shows across the small towns in Maryland. Every end of year, the town lights up during the Winter City Lights festival, which features at least a million twinkling lights across 18 acres, transforming the area into a glowing winter wonderland. This is a time for everyone to gather around a bonfire and share fun stories, admire the town's 52-foot Christmas tree, and enjoy refreshing hot chocolate and fresh pizza. Olney's thriving performing arts scene is headquartered at the Olney Theatre Center, where fans from around the region come to watch a year-round showcase of premier plays and musicals.
Beginner and intermediate golfers have an opportunity to perfect their swing and learn valuable golfing techniques at the Olney Golf Park. This high-quality facility features a performance golf academy where guests can attend lessons, enroll in camps, and work with a professional trainer.
Chestertown
This historic colonial port town provides a vivid reminder of life at the height of colonization along the East Coast. Walking around the Chestertown Historic District allows guests to view an expansive stretch of 18th- and 19th-century buildings, providing an exciting journey through time. The neighborhood hosts the annual Chestertown Tea Party Festival, which honors the community's acts of revolution against British taxation during the 18th century. The festival features an array of activities, including vivid reenactments, craft vendors, live music, a colorful parade, and celebrations along the river.
Chestertown is renowned for its vibrant arts community, which welcomes tourists to support, celebrate, and be inspired by the creativity showcased at the Garfield Center for the Arts. Seating an audience of 200-250 people, this delightful hub showcases a lineup of contemporary productions and classic plays in an intimate venue. The theater is wheelchair accessible, offering an inclusive atmosphere for everybody in the town to gather for the arts.
Hagerstown
Hagerstown offers a diverse array of experiences that you won't find anywhere else in the region. The town is home to the Hagerstown Aviation Museum, where a stunning collection of historic planes highlights the advent of American aviation. The museum features over two dozen landmark artifacts preserving a century of aviation heritage, while honoring pioneers like Glenn Curtiss. Art enthusiasts get the best out of watching stage performances at the Maryland Theatre. The massive 1910s venue accommodates more than 1,200 guests, lured by the chance to witness professional acts like the Symphony Orchestra, the Hagerstown Community Concert, and the Barbara Ingram School for the Arts.
The Pennsylvania Dutch Market offers a unique cultural experience, where Amish and Mennonite merchants showcase their fresh farm produce and baked goods for vacationers to purchase. From Amish furniture and pies to cheese and seafood, it is the perfect gathering to mingle with townsfolk.
Whether tasing Maryland's official state desert in Smith Island or partying on the sandy beaches of Ocean City, these unforgettable small towns to visit in Maryland showcase how diverse and surprising the state can be. From historic ports and mountain gateways to quiet waterfront villages and vibrant arts hubs, each town offers experiences you truly can’t find anywhere else in the country. Together, they open your eyes to what makes the state so unique and a must-see stop on the East Coast of the United States.
