5 Most Charming Small Towns in Maryland

Maryland is home to numerous charming and picturesque small towns, each with its own unique character, history, and attractions. Here are a few notable small towns in Maryland:

5 Most Charming Small Towns in Maryland
5 Most Charming Small Towns in Maryland

St. Michaels

Located on Maryland's Eastern Shore, St. Michaels is a quaint waterfront town known for its historic charm. It's a popular destination for boaters and history enthusiasts. The town features beautiful 19th-century architecture, boutique shops, and excellent seafood restaurants. The Chesapeake Bay Maritime Museum is a major attraction here.


Located on the Eastern Shore, Berlin is often considered one of America's coolest small towns. It has a well-preserved historic district with Victorian architecture, tree-lined streets, and a lively arts scene. The town is known for its role in the movie "Runaway Bride."

Havre de Grace

Situated at the confluence of the Susquehanna River and the Chesapeake Bay, Havre de Grace is a charming town with a maritime history. It offers scenic views, a promenade along the waterfront, and a lighthouse. The town is known for its seafood and is a popular spot for boating and bird-watching.


Located on the Eastern Shore, Chestertown is a historic town known for its colonial-era architecture. It's home to Washington College, which adds a youthful vibrancy to the town. Chestertown hosts various events and festivals, including the popular Tea Party Festival.

Ellicott City

Nestled in the rolling hills of Howard County, Ellicott City is known for its historic district, featuring picturesque, historic buildings, antique shops, and restaurants. It's also known for its charming Main Street, which often hosts events and festivals.