11 Most Welcoming Small Towns in Maryland


Maryland offers a variety of attractions including charming small towns, rich history, culture, nature, and seafood, making it an ideal destination for travelers.

Where history meets innovation, creating timeless stories in the heart of the Chesapeake Bay.

A quaint town where the Chesapeake Bay meets the Susquehanna River, Havre De Grace offers scenic waterfront views, a historic lighthouse, and a boardwalk with museums and parks.

Havre De Grace


A charismatic harbor town with a rich maritime heritage, St. Michaels features a 19th-century lighthouse, a maritime museum, a distillery, and a variety of water activities.

St. Michaels


A small town nestled in the Catoctin Mountains, Thurmont is a gateway to nature and adventure.



A colonial town on the banks of the Chester River, Chestertown boasts a historic district with elegant buildings, a lively arts scene, a farmers market, and a riverfront park.



One of the oldest towns in Maryland, Oxford is a peaceful retreat on the Eastern Shore.



A vibrant town with a mix of old and new, Easton offers something for everyone.



A historic town that was once the capital of Maryland, St. Mary’s City is a living museum of the colonial era.

St. Mary’s City


A charming town that was named the coolest small town in America, Berlin is a popular destination for movie fans, as it was featured in films like Runaway Bride and Tuck Everlasting.



A cozy town that was voted the best main street in America, Sykesville is a place where you can feel at home.



A historic town that survived several floods, Ellicott City is a testament to resilience and perseverance.

Ellicott City


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