6 Most Laid-Back Small Towns In Maryland

With its coastline along the Chesapeake Bay and Potomac River, Maryland offers a laid-back, coastal lifestyle. Cities with pristine boardwalks, waterfront restaurants, calm harbors, and historic canals are a few of the hidden treasures that await its visitors. Additionally, as one of the original thirteen British colonies and US states, Maryland has a rich and fascinating history, with many colonial-style buildings, lighthouses, and museums to explore. When you need an escape from the city, don't hesitate to visit one of these scenic, historic towns where relaxation comes naturally.

North Beach

Sitting along the western shore of the Chesapeake Bay, North Beach has a beautiful boardwalk, fishing pier, and waterfront to explore. Due to the town’s small size, essentially everything a traveler could need is within walking distance of the beach, pier, and boardwalk, including gift shops, ice cream shops, art galleries, and an array of dining options. Additionally, in the warmer months, from around April through October, the town hosts a weekly farmers market on Saturdays, giving visitors the chance to truly experience the town’s warm and friendly atmosphere as well as buy some delicious baked goods, cheeses, meats, and more.

Located on the edge of town is Wetlands Overlook Park, a small nature park filled with wetland wildlife and migratory fowl. It also has a pier and two gazebos that make it a wonderful place to rest while appreciating the views. A visit to North Beach is not complete without stopping by its interesting Bayside History Museum, which thoroughly and thoughtfully explains the history of the communities that reside along the Chesapeake Bay.

Hancock

As one of Western Maryland’s oldest settlements, Hancock is brimming with history to explore, dating back to as early as the 18th century. Visitors can immerse themselves in Hancock’s story by visiting the historic Bowles House, which exhibits the town’s history through a well-maintained farmhouse from the 1780s, which maintains a lot of its original 18th-century feel. Visitors can further explore the town’s history by seeing town archives in the Hancock Historical Society Museum as well.

The town is home to several beautiful natural landmarks, including the C&O Canal, which was once a vital transportation route in the early 19th century and now offers breathtaking views from its trails. Visitors can also get out on the Potomac River and enjoy a relaxing afternoon fishing or boating on the calm waters.

St. Michaels

Frequently voted as one of the country’s best coastal towns, St. Michaels is the perfect escape for city folk, especially due to its proximity to metropolises such as Washington D.C., New Jersey, and Philadelphia. Its harbor makes it a great place to enjoy a variety of water activities, such as cruises, sailing charters, paddleboarding, and kayaking. After spending the day out on the water, hungry travelers have plenty of options for a good meal, such as Bistro St Michaels, which offers French-inspired cuisine, creative cocktails, and an impressive wine list, or The Oak Room, a waterfront fine dining restaurant, which also happens to be a luxurious hotel!

The town has a good selection of museums as well, such as St. Michaels Museum at St. Mary's Square, which dives into the town’s history, and the Chesapeake Bay Maritime Museum and Store, which shares the Chesapeake Bay’s maritime history in more detail. For those who love automobiles and motorcycles, make sure to stop by the Classic Motor Museum, which has an excellent array of classic vehicles on display!

Leonardtown

Leonardtown, along the McIntosh Run River, is a beautiful, walkable town along the water with an abundance of local restaurants, shops, and art galleries. In fact, it's the only town in southern Maryland with an Arts & Entertainment District approved by the Maryland State Arts Council. Within its Arts & Entertainment District, visitors can stroll through its many art galleries, attend art shares with renowned artists, take art classes, or attend a workshop.

The town also inaugurated the Butterfly Trail in 2021, which will lead visitors around various important sights in town and pass by various contemporary-style artworks from local artist Eric Clark Jackson. To travel from one landmark to the next more easily, visitors can also take the charming Leonardtown trolley, which runs for free in the summers and makes stops in several important town landmarks.

Cumberland

Cumberland, known as the “Gateway to the West,” is located in the Maryland mountains. It has tree-lined streets, an artsy atmosphere, and welcoming residents. For those wanting to venture outside of the city, Dans Mountain State Park is just a twenty-minute drive southwest. It is a 481-acre park on a 16-mile-long mountain. In addition to its wonderful views, the park has an Olympic-sized swimming pool, recycled tire playground, four pavilions, and a fishing pond, making it the perfect place to unwind for an afternoon.

Within the city's downtown, visitors can relax by sipping a refreshing red, white, or fruit wine at Charis Winery or catch a musical or drama at the local Cumberland Theatre. The town also hosts a variety of cultural events throughout the year worth checking out, such as Delfest, which takes place in the spring and showcases the best of McCoury music in a fairground along the Potomac River.

St Mary’s City

Previously a colonial town founded in 1634, St. Mary’s was one of the first European settlements in the state. It is now filled with museums, historic churches, lighthouses, American War sites, and more. Visitors can stop by St. John’s Site Museum, a free exhibit, to see an excavated original site from the 17th century and several artifacts from the time period. Afterward, they can explore the Woodland Indian Hamlet, which allows visitors to explore and learn about the lifestyle of the Yaocomaco indigenous people through interactive experiences.

After exploring St. Mary’s historic sites, visitors can drive a short way away to one of the area’s nearby farmers markets, such as the California Farmers Market in California, The Home Grown Farmers Market in Lexington Park, or the Barns at New Market in Mechanicsville. Following a relaxing stroll through one of the farmer's markets, visitors can explore local shops with a charming farm atmosphere, including dairy stores, country shops, and quilt boutiques.

Final Thoughts

Although Maryland is one of the smallest states in the US, its impressive hidden treasure towns should not be ignored. Historic colonial sites, natural parks, elaborate art districts, and maritime culture are just a few of the highlights that many of these towns have to offer. Additionally, the small size of these towns makes them easy to explore while still being able to have a relaxing, laid-back vacation. Next time you are craving a breath of fresh air and a change of pace, be sure to keep these six towns on your radar!