6 Best Towns in Maryland to Visit in 2026

As one of the original colonies, Maryland wears its history proudly; this is the birthplace of America's National Anthem, after all. But the Old Line State isn't just a greatest-hits album of the past. Think Chesapeake Bay views, piles of blue crabs, and that easy, welcoming charm that makes you want to linger a little longer. The best way to feel all of it? Get out of the cities and wander through Maryland's small towns.

From postcard-pretty fishing villages to the mountain hideaways around Oakland and the sun-soaked boardwalks of Ocean City, these places are the state's heartbeat. Whether it's your first Maryland trip or you're coming back for another round, they're perfect for a weekend escape. And yes, there are a lot of options. To make it easier, here are some of the most exciting small towns in Maryland to add to your next travel itinerary.

Oakland

Located in Garrett County, Oakland is ideal for those who enjoy weekend escapes with fresh air. The town offers access to some of Maryland's most scenic wilderness, providing plenty of space to unwind and breathe. The highlight is Swallow Falls State Park, featuring tranquil trails, secluded picnic areas, and the impressive 53-foot Muddy Creek Falls. For a more immersive outdoor experience, stay overnight at Wild Yough Glamping Huts and sleep under a starry sky.

When you're ready for a change from hiking to exploring history, Oakland has that covered too. The Garrett County Historical Museum showcases generations of local life through artifacts and exhibits that bring the past to life. Enthusiasts of trains should visit the Oakland B&O Railroad Museum, filled with pieces of the area's railway history. Planning ahead? Don’t miss the Autumn Glory Festival in October, a five-day event with a grand parade, crafts, music, and car shows that bring Oakland and nearby areas to life.

Ocean City

If your ideal escape involves salty air and sandy toes, Ocean City is the place to be. This classic resort town lies between the Atlantic Ocean and Isle of Wight Bay, offering stunning water views. Begin with a walk along the historic Ocean City Boardwalk, which combines nostalgia with a lively atmosphere filled with food carts, souvenir shops, and street performers. Then, head over to the 10-mile Ocean City Beach, where the expansive shoreline is perfect for swimming, sunbathing, and relaxing until sunset. Need a break from the sand? Visit the Ocean City Life-Saving Museum to explore stories of daring rescues and local maritime history. Art enthusiasts can enjoy rotating exhibits at the Art League of Ocean City, a contemporary gallery featuring local artists. For water adventures, West OC Watersports offers relaxed trips like dolphin and pony tours around Assateague Island.

Centreville

Centreville, located on Maryland's Eastern Shore, offers a mix of history, small galleries, and enough nature to keep weekends outdoorsy. Situated along the Corsica River between Chestertown and Easton, it is surrounded by peaceful, green landscapes. For a leisurely stroll, try the Conquest Preserve Trailhead, which winds through woods to a quiet beach—perfect for wildlife viewing and relaxing. If you're interested in rural Eastern Shore life, the Queen Anne's Museum of Eastern Shore Life is a great stop. It features antique farm equipment, old tools, and relics that give insight into how the town's residents lived and worked in the past.

Cambridge

Cambridge seamlessly combines maritime history, Eastern Shore traditions, and water-based recreation. Nautical references are visible throughout the town, with the Choptank River Lighthouse standing out as a perfect photo spot, especially with the marina nearby adding postcard-worthy scenery. To explore the region's on-the-water legacy further, visit the Richardson Maritime Museum, which features artifacts from watermen and working boats, illustrating centuries of life along the river and bay.

Nature enthusiasts should set aside time for the Blackwater National Wildlife Refuge, a vibrant area of forest, marsh, and shallow waterways. It's a sanctuary for waterfowl, nesting bald eagles, and migrating birds—bring binoculars if possible. For a meaningful glimpse into local and national history, consider the guided walking tours by the Harriet Tubman Museum and Education Center. Be sure to check their website for reopening updates, as the museum is temporarily closed for renovations due to water damage.

Annapolis

Annapolis, Maryland's capital, is also one of the easiest places to experience a bit of time travel without much effort. Its historic district boasts charming 18th-century brick buildings, with the Maryland State House—built in the 1700s—standing out. As the oldest still-in-use state capitol, touring it feels like stepping back into early American history. You can continue exploring history at the United States Naval Academy, where waterfront grounds, monuments, architecture, and museum exhibits create a surprisingly scenic afternoon.

When it's time to relax, Quiet Waters Park offers a perfect retreat. Covering 340 acres along the South River, it's ideal for picnics, nature walks, boating, and leisurely people-watching. No visit is complete without experiencing Annapolis' sailing culture at the City Dock, the hub of local events. Watch for the Annapolis Spring Sailboat Show, an annual late-April event that fills the harbor with sailboats, gear demos, and plenty of on-the-water sights.

Bel Air

Bel Air, the county seat of Harford County, offers an easy-going planning experience with a touch of history, nature, and activities. Located conveniently between Baltimore and Philadelphia, it serves as a perfect quick escape from either city. For scenic views, explore the Ma & Pa Heritage Trail, a multi-use path spanning about 3.3 miles in Bel Air and an additional 1.7 miles in Forest Hill, passing through forests and along creeks with pastoral vistas that feel far from urban chaos. For those interested in historic homes and local tales, visit the Hays House Museum, the oldest building in Bel Air from the 18th century, providing a glimpse into the town's early history.

If you're traveling with children or seeking playful fun, Jurassic Golf and Arcade is a great option. The dinosaur-themed mini golf course and arcade feature animated prehistoric scenes, roaring dinosaurs, and vibrant chaos that keep the entire family entertained.

Whether you're hunting for overlooked history, craving a day on the sand with Atlantic views, or itching for an outdoorsy reset, Maryland's small towns make a strong case for your upcoming travel plans. They're proof that some of the state's best experiences live outside the biggest cities, quieter, friendlier, and easier to savor. This year, consider linking a few towns together into one trip so you can see just how many different "Marylands" are waiting across the countryside.