8 Underrated Maryland Towns Worth the Drive in 2026

Maryland packs in everything from Chesapeake Bay shoreline and crab-house waterfronts to colonial-era main streets scattered across the Eastern Shore. Places like Hyattsville buzz with arts venues and eateries, while Cumberland offers access to the Great Allegheny Passage Trail alongside charming historic streets. Along the bay, Leonardtown and North Beach feature marinas, seafood shacks, and unforgettable sunset views. Together, these eight underrated Maryland towns show that some of the state’s most memorable experiences are well worth the drive.

Hyattsville

Just north of Washington, DC, and part of the DC metro area, is a small community called Hyattsville. Visitors can explore the Pyramid Atlantic Art Center, which specializes in papermaking, book art, and print art. The same center hosts the annual Hyattsville Arts & Ales Festival in September, which welcomes about 100 local artists and craft makers, along with food vendors and live musical performances.

The downtown area is brimming with a lot of charm, too. During the summertime, the Hamilton Splash Park opens with its aqua climbing wall. Streetcar 82 Brewing Co., a deaf-owned business, named itself after a streetcar line that started service in 1888 and ran for the next 80 years. According to the business' website, the brewery staff is comprised of people who are deaf, and they prioritize working with deaf contractors. They have a wide selection of brewed beverages for your perusal and enjoyment.

Brunswick

Beginning in the late 2000s, according to Neilsberg Research, the town's population has grown more than 30%, bringing new residents, new employers, and new development — efforts you can see in the various shops that have sprung up. Beans in the Belfry is a local cafe that was once a 20th-century church. There you can grab a nice cup of coffee, lunch, or listen to live musical performances.

The surrounding area makes Brunswick a great place to explore. The C&O Canal National Historical Park is one of the most-visited national parks in the United States. There's also the Brunswick Heritage Railroad Museum; it showcases the important history of the Baltimore and Ohio Railroad in Frederick County. There's even a celebration of railroad heritage with Railroad Days. Held every October, the community gathers at the banks of the Potomac River for local performances, artists, artisans, model train displays, and food and drink.

Cumberland

Boasting one of the largest communities in the western part of the state, Cumberland is located in Maryland's panhandle. The Great Allegheny Passage Trail begins in Cumberland at Mile Marker 0 and offers 150 miles of cycling that stretches all the way to Pittsburgh, Pennsylvania. The local shops and restaurants can also pull you in for excellent food and fun experiences. Ristorante Ottaviani, a highly rated Italian restaurant, serves classic Italian dishes, for example. For a taste of history, you can see one of George Washington's many headquarters. Throughout the Revolutionary War, he used several, but this one has been beautifully preserved.

Leonardtown

In the heart of St. Mary's County and along Breton Bay is Leonardtown. The town has a relaxing and peaceful vibe, and it's a highly walkable town. The annual End of Summer Beach Party Blowout involves a manmade beach made of 40 tons of sand that's placed in the center of town. The shops also have their own vibes and specialties, such as Heritage Chocolates, a store dedicated to handmade chocolate and candy confections. You also don't want to miss the Alice in Leonardtown Mural and Wine and Design, a local painting studio that routinely offers art classes and private parties.

Frostburg

A lively college town, Frostburg is a mountain destination providing access to the Great Allegheny Passage, a 16.3-mile-long trail that stretches all the way to Cumberland. The terrain is perfect for hikers, walkers, and cyclists. Another place to explore is the Western Maryland Scenic Railroad. The railroad and trains were recently restored and operate year-round while offering interesting experiences, including seasonal excursions, dinner trains, and Hands-on-the-Throttle experiences. For one final taste of history, the Frostburg Museum explores local history and is within walking distance of hotels, restaurants, and shops.

North Beach

The town of North Beach is a coastal town that provides ample reasons to visit, with events like Christmas at the Beach, a month-long festival featuring bright lights, big displays, campfires, a market, a parade, and Santa-themed activities for the kids. North Beach's shoreline, pier, and pavilion are welcoming spots for summer recreation, featuring bike paths, benches, pier fishing, and beautiful views of sunrises and sunsets. Exploring the walkable downtown will grant you delicious meals, great drinks, and an energized community. Neptune's Seafood Pub is a popular community gathering spot with a laid-back and neighborhood vibe.

Chestertown

Tucked on the eastern shore of the state, Chestertown is a treat. Close to the international airport in Baltimore, the town is an arts and culture hub. If you stay the night, the charming White Swan Tavern is a good choice; it's a historic bed and breakfast in a Colonial-era building near downtown. Keeping to the Colonial history, Chestertown also hosts the Chestertown Tea Party Festival. A celebration of the famous Revolutionary-era protest in 1774, the festival in late May reenacts the moment along with walking tours of the district, live demonstrations of how handcrafted Colonial goods were made, and a 10 Mile Run or 5K Run/Walk.

Another remarkable place that ties the community together is Washington College. Boasting a rich history with George Washington himself, the college holds the distinction of being the first college chartered in the sovereign United States. The college hosts many exhibits and public lectures.

Thurmont

Nicknamed "the Gateway to the Mountains," Thurmont has a lot to explore and appreciate. A good sampling of this is exploring the Catoctin Mountains, which has 25 miles of trail for you to explore. Another remarkable park to consider is the Cunningham Falls State Park, displaying the state's tallest waterfall and plenty of swimming and boating spots. (Note that you can only swim from Memorial Day until Labor Day.) Finally, there's the Catoctin Colorfest, a two-day arts and crafts show held annually during the second full weekend of October. The event started back in 1963 and regularly draws more than 100,000 people.

From the cascading waterfalls of Thurmont’s Cunningham Falls State Park to the historical Tea Party Festival in Chestertown and the scenic trails of Frostburg’s Great Allegheny Passage, these towns showcase just a fraction of Maryland’s hidden treasures. Many are conveniently located within driving distance of major cities like Washington, DC, and Baltimore, making them ideal for day trips or weekend getaways. Whether you’re seeking history, nature, or small-town charm, Maryland’s underrated towns offer experiences that are truly worth discovering.