17 Historic Towns in Maryland That Will Take You Back in Time

Maryland may be tiny, but there are a surprising amount of places to explore here. As the seventh state, there’s plenty of history to uncover. Take a drive around this small state and discover some of its hidden historical gems. 

1. Chestertown

Chestertown Public School Building, currently used as a Kent County government building.
Editorial credit: grandbrothers / Shutterstock.com

On the Eastern Shore of Maryland, you’ll find Chestertown. Chestertown was once a major colonial port and was founded in 1706. A lot has changed since then, but many of the town’s historic buildings still remain. 

One of the oldest houses is the River House, built between 1737 and 1743. Like many of the historic homes in the area, the interior is decorated in a Georgian style, featuring grand entrances and intricate molding.

Walking around these old homes will really make you feel like you’re in another century.

2. Easton

The intersection of Dover and Washington Streets, in Easton, Maryland.

Drive an hour south and you’ll hit the town of Easton. Originally settled by the Quakers in 1682, Easton still maintains its historic charm. Take a walk down Washington Street and enjoy the quaint shops and cozy cafes.

If you really want to take a step back in time, visit the Third Haven Meeting House. The main building of this church was originally built in 1684. Although some renovations and additions have been added, parts of the original structure still stand. 

3. St. Michaels

Old wooden lighthouse near the port of St Michaels Maryland USA with blue cloudy sky

If you’re looking for more historic towns in Maryland, you’ll find another one just west of Easton. St. Michaels is a quaint waterfront town known for its shipbuilding industry. Its history dates all the way back to the 1600s, when it served as a trading post for local tobacco farmers and trappers.

You can still explore some impressive historic landmarks, including the 1879 Hooper Strait Lighthouse, the Cannonball House, and several interesting museums.

If you’re looking for a deeper knowledge of the local history, The Patriot Cruise offers a guided tour on a 2-level cruise boat.

4. Cambridge

iew of historic buildings in Cambridge, an old colonial fishing town in Dorchester County, Maryland, United States
Editorial credit: EQRoy / Shutterstock.com

Head south and you’ll find the historic town of Cambridge, which dates back to 1684. Like many towns in this area, Cambridge has a rich maritime heritage. Its location along the Choptank River and its wonderfully preserved architecture make it a stunning place to visit. 

Take a walk down High Street and you’ll spot houses from the 1700s and 1800s. Wander a bit more and you’ll find a Gothic church dating back to 1684, a windmill that’s hundreds of years old, and several museums celebrating notable events and people. 

5. Berlin

Main Street sign post, Berlin, Maryland, with brick building in soft focus in the background.

Just a short drive from the famous beaches of Ocean City, you’ll find the quiet town of Berlin. Its historic Main Street features nearly two centuries of architectural heritage, including buildings from the Federal and Victorian eras. 

Dotted between the impressive historical landmarks are cute shops and restaurants that make visiting Berlin a real treat. Whether you’re interested in history or just appreciate a town that feels historic, Berlin is the place for you. 

6. Havre de Grace

Buildings opening onto street in small town of Havre de Grace in America.

At the northern tip of the Chesapeake Bay, there’s Havre de Grace. This cozy town was first incorporated in 1785. It was known for its oyster and crab harvesting and also served as an important stop along the Underground Railroad.

There are various museums and landmarks to visit, but make sure to stop in the famous Historic District. This area is home to about a thousand buildings from the 18th, 19th, and early 20th centuries. There’s even a website where you can explore the specific history of about 450 different historic buildings. 

7. Annapolis

The historic chapel at the US Naval Academy in Annapolis, Maryland.

While it’s definitely not a small town, Annapolis is certainly a historic one. Since 1694, this has been a popular place for sailors and scholars alike. There are so many buildings and streets that hold the history of this treasured capital city. 

The most famous would be the Maryland State House, which has been in use since 1783. There’s also the United States Naval Academy, which has been training our military since 1845. Even before that, St. John’s College served as a higher education facility and can trace its roots back to 1696. 

8. London Town

Close up of hands demonstrating how a musket works from a man in Colonial military uniform.

A bit further down the western coast of the bay, just outside the popular city of Annapolis, is London Town, Maryland. This 100-acre town was established in 1683 as an important trade port. While it’s no longer an official town, it still has lots of exciting history to explore. 

The Historic London Town and Gardens offers guided tours for visitors to learn all about the area’s unique maritime history. You’ll find people in period-appropriate clothing, musket fire demonstrations, and plenty of historic reconstructions that will bring you back in time. 

9. Ellicott City

 The Ellicott City Historic District lies in the valleys of the Tiber and Patapsco rivers. Many of its buildings were constructed in the 1800s.
Editorial credit: Nicole Glass Photography / Shutterstock.com

Maryland’s most popular historic town is located right in the middle of the state. Every year, people from all over the country flock to Ellicott City for its historic charm. From adorable Old Ellicott City shops and cozy cafes to historic sites and interesting museums, there’s something for everyone.

The Ellicott City historic district is one that will definitely take you back in time. It’s been around since 1772, and although many of the buildings have been renovated, it still maintains that old-timey feel. 

10. Frederick

Historic Downtown Frederick Maryland sign in downtowan area.
Editorial credit: George Sheldon / Shutterstock.com

As you make your way towards western Maryland, you’ll encounter the old town of Frederick. It’s one of the largest cities in Maryland, and it was founded in 1745 by German and English settlers. You can still see some of that influence today in the restored historic homes.

Even the visitor center brings some historical charm, as it’s housed in a renovated canning warehouse from the 19th century. Start there, then wander through downtown Frederick to get a look at several interesting structures and statues commemorating the rich history of this town.

11. Oldtown

C&O Canal, Near Washington DC (Along the Potomac River)

It’s fitting that a place named Oldtown would make the list of small historic towns in Maryland. This area in western Maryland was originally established in the 18th century as a Shawnee Amerindian village. After being abandoned for decades, it was established as a trading post in 1741.

Not much of the original town remains, but you can still visit the Michael Cresap House. It gives you an inside look at the role this town played in early American trade routes. You can also check out parts of the Chesapeake and Ohio Canal, which served as an important waterway for nearly 100 years.

12. Cumberland

Western Maryland Railroad steam train
Editorial credit: Steve Heap / Shutterstock.com

Keep driving west and you’ll come across the town of Cumberland. This town dates back to 1787, when it was a major industrial and transportation hub. It was so important that it was even called “The Queen City.”

Now, however, Cumberland is much quieter. The hustle and bustle of the old days is gone, but some of the history still remains. One popular historical attraction that will take you back in time is the Western Maryland Scenic Railroad, which offers several different themed rides on a vintage train. 

13. Oakland

The Baltimore and Ohio Railroad Red Train Car founded 1828 by John W. Garrett and William Patterson
Editorial credit: Kim Howell / Shutterstock.com

If you go all the way to the western edge of the state, just before you hit West Virginia, you’ll run into Oakland, another one of many historic towns in Maryland. Although it wasn’t incorporated until 1862, there’s still plenty of history here.

The B&O railroad station is the town’s most prominent destination, but there are also several churches that have stories to tell. St. Matthew’s Episcopal Church and St. Peter the Apostle Church are both key places to visit for religious history buffs.

14. St. Mary’s City

John's Site Museum at Historic St. Mary's City
Editorial credit: Regine Poirier / Shutterstock.com

Head down to the southern tip of Maryland and you’ll find the historic gem of St. Mary’s City. This former colonial town was the state’s first European settlement and capital. While not many of the original buildings remain, most have been rebuilt so people can experience the town as it once was.

There are churches, state houses, museums, and even people dressed in period-appropriate clothing to really make you feel like you’ve taken a step back in time. You can explore the colonial settlement, as well as a recreation of the Woodland Indian Hamlet, which depicts the lives of the local Yaocomaco people. 

15. Emmitsburg

The seminary at Mount Saint Mary's University, in Emmitsburg, Maryland.

At the very top of the state, less than a mile from the Maryland-Pennsylvania border, you’ll find the small town of Emmitsburg. Originally settled in 1733, Emmitsburg is now mostly known as the home of Mount Saint Mary’s University, the oldest private independent Catholic college in the country.

When you’re done exploring the campus, there are plenty of other stunning religious sites in Emmitsburg with historical significance. One of the most popular is the National Shrine of St. Elizabeth Ann Seton. Although it was built in modern times, the decor will instantly transport you back to the 18th century. 

16. Boonsboro

Washington Monument State Park

Not too far from Emmitsburg, you’ll find the town of Boonsboro. This rural town was founded by two brothers, George and William Boone, in 1792. Although the town didn’t grow to be as big as the brothers had hoped, it still remains as one of the most charming small historic towns in Maryland.

The Bowman House is a stunning example of the local architecture, as is the Inn BoonsBoro. History buffs can head to the local Museum of History, which contains artifacts from the Civil War.

And for those looking for a bit of history and adventure, you can hike to the summit of South Mountain and check out the monument to George Washington. 

17. Port Tobacco

National Historic site of home of Thomas Stone, signer of Declaration of Independence

As the smallest incorporated town in Maryland, with a recorded population of only 13 people, Port Tobacco is definitely not the liveliest place in the state. But that doesn’t mean it’s not filled with plenty of amazing historical treasures. 

In fact, in the 17th century, this area was once the site of one of the largest settlements in Maryland. Times have certainly changed, but reminders of the heyday still remain.

You can visit several 18th-century homes, a one-room schoolhouse from 1876, and the home of Thomas Stone, one of the original signers of the Declaration of Independence. 

Annapolis, Maryland, USA downtown view over Main Street with the State House.

From tiny towns to capital cities, there are lots of historic towns in Maryland. Just take a drive around and explore the many stories that are told by these unique places. What’s your favorite small historic town in Maryland?

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