Taking a Tour of Maryland’s Historic Cities

Maryland, one of America’s original thirteen colonies, is steeped in rich history that dates back centuries.

From its colonial roots to its crucial role in the Civil War, the state’s past is etched into its landscape, especially its historic cities.

But here’s the issue:

Maryland isn’t typically a state that gets the ‘limelight’ where sightseeing is concerned.

And the reason for this is simply because it tends to be ‘overlooked’ when people look at states like Las Vegas, New York, Florida, etc.

These are states that get a lot more ‘vacation destination fanfare’ than Maryland.

But in this post, you’re going to learn why Maryland is actually an overlooked gem from a sightseeing and vacation perspective—especially when it comes to its historic cities.

So in this guide, you’re going to learn about some of Maryland’s most historically significant cities and what they offer to those eager to step back in time.

1. Annapolis

State Capital since 1694.

Description: Often referred to as the “Sailing Capital of the U.S.,” Annapolis is home to the prestigious United States Naval Academy. Its vibrant Historic District boasts 18th-century brick homes, narrow streets, and significant colonial landmarks.

  • Highlight: The Maryland State House, the oldest in continuous legislative use in the U.S.
  • Activities: Stroll through the Historic District, visit the Naval Academy, or take a guided walking tour to delve deep into the city’s past.

2. Frederick

Established in 1745.

Description: Nestled at the crossroads of major Civil War campaigns, Frederick is a blend of historic sites, art venues, and a thriving culinary scene.

You may never see a city as beautiful as this in the fall. It’s truly breathtaking and definitely worth a visit!

  • Highlight: The Historic District, with 50 square blocks of well-preserved 18th and 19th-century architecture.
  • Activities: Explore the National Museum of Civil War Medicine, walk along Carroll Creek Park, or indulge in local gastronomy at Market Street.

3. St. Mary’s City

Maryland’s First Capital.

Description: As the site of Maryland’s first colonial settlement and capital, St. Mary’s City is a living history museum that showcases the state’s early days.

This isn’t just a beautiful and historic city in Maryland, either. It’s technically Maryland’s oldest city. Thus, it tells an important story about the history of not only the state of Maryland, but also the entire United States as a whole.

  • Highlight: Historic St. Mary’s City, a large outdoor museum.
  • Activities: Witness reenactments, explore reconstructed colonial buildings, and visit the Maryland Dove, a replica of the ship that brought the first settlers.

4. Chestertown

Founded in 1706.

Description: Located on the banks of the Chester River, Chestertown is a colonial port town known for its historic homes, waterfront, and the annual Chestertown Tea Party Festival.

  • Highlight: Washington College, the tenth oldest college in the U.S.
  • Activities: Attend the Tea Party Festival, explore the Historic District, or embark on a river cruise.

5. Ellicott City

Established in 1772.

Description: This picturesque mill town, set along the Patapsco River, showcases a charming blend of historic sites and modern amenities.

  • Highlight: The B&O Railroad Station Museum, the oldest surviving railroad station in the U.S.
  • Activities: Wander through the Historic Main Street, visit the Patapsco Valley State Park, or discover unique antiques and artifacts in local shops.

6. Hagerstown

Founded in 1762.

Description: Positioned near Civil War battlefields, Hagerstown offers a rich tapestry of history, arts, and culture.

  • Highlight: Hagerstown’s Arts and Entertainment District.
  • Activities: Explore the Washington County Museum of Fine Arts, take a walking tour of the city’s historic homes, or relive history at the nearby Antietam National Battlefield.


A journey through Maryland’s historic cities is more than just a trip; it’s a voyage through time.

Just keep in mind that if you want to enjoy some medical cannabis while you’re on your trip, you’ll need to get your medical card well in advance.

Websites like this make it super easy to set up quickly, so you can get on with your trip and enjoy the sights without worrying about cannabis legalities.

Each city, with its unique story and preserved landmarks, offers a window into different chapters of American history.

From cobblestone streets echoing with tales of the past to buildings that witnessed pivotal moments, Maryland invites you to discover its legacy.