
ANNAPOLIS, Md. — Maryland’s history isn’t just found in museums — some of it is still standing. While countless structures from the Old Line State’s earliest days have disappeared, a remarkable few have survived for centuries, offering a rare glimpse into the Maryland of the past. From historic homes and churches to forts and other landmarks, we’ve compiled some of the oldest pieces of architecture from each region of Maryland. Get ready to discover the buildings that have stood the test of time and the history behind them.
Southern Maryland – Brooke Place Manor

Often referred to as one of Maryland’s oldest surviving buildings, Brooke Place Manor in St. Leonard was originally built by former acting governor of Maryland Robert Brooke Sr. The structure was first constructed around 1652 to serve as a private residence, and its original structure partially remains standing to this day.
Brooke Place Manor was renovated in the 1800s, and reportedly, only the lower section of the exterior wall remains of the original structure. Regardless, Brooke Place Manor earns its reputation due to its incredible age, honoring a former governor centuries after his death.
This historic house in Southern Maryland has been passed down to many owners over its nearly 400 years of existence. Today, Brooke Place Manor is privately owned, so unlike many other historic buildings, it hasn’t become public property.
Western Maryland – Jonathan Hager House

Constructed around 1740, the Jonathan Hager House in Hagerstown is a relic of a time long past. It was built by German immigrant Jonathan Hager, founder of Hagerstown, and has survived until today through regular maintenance and renovations.
Hager eventually sold the historic house to Jacob Rohrer, and it stayed in his family until the Washington County Historical Society gained ownership in the 1940s, after which ownership was then passed down to the city of Hagerstown. The Jonathan Hager House is a limestone homestead that was purposefully built over springs to provide fresh water to its inhabitants.
Today, visitors can take a tour of the Jonathan Hager House complete with fascinating artifacts and historically relevant furniture. This German Colonial house is one of Western Maryland’s most important pieces of architecture, and its lengthy history is overshadowed only by its distinct appearance.
Maryland’s Eastern Shore – Old Trinity Church

Maryland’s Eastern Shore is packed full of historic structures, but the Old Trinity Church is documented as one of the oldest. Built in the late 1600s, the Old Trinity Church serves an Episcopal community that still holds services to this day.
Old Trinity is documented as one of the oldest operating Episcopal churches in the United States, granting it a spot among Maryland’s most historic architecture. Furthermore, the “Old Graveyard” at Old Trinity Church has existed since colonial days, with veterans from various American wars buried under its soil.
The red brick structure known as the Old Trinity Church is an important monument on the Eastern Shore, and its continuous use hundreds of years after its original construction is a testament to this building’s importance to the local community.
Maryland’s Capital Region – Old Spring House

It’s commonly reported that English colonists built the Old Spring House around 1683 atop a natural spring, though the exact timeline is up for debate. This modest structure sits within the Fort Lincoln Cemetery, and in its day, the Old Spring House helped to preserve dairy products like milk and butter, an invaluable resource in the 1600s.
Though the Old Spring House is on the smaller side, this Prince George’s County structure is one of the oldest remaining buildings in Maryland’s Capital Region. Contemporary history fans can visit the Fort Lincoln Cemetery to see the Old Spring House in person, as it remains standing hundreds of years after its construction.
The Old Spring House goes to show that even the smallest structures with the most mundane purposes are often among the most noteworthy, as its ability to preserve dairy was of the utmost importance to early settlers.
Central Maryland – Fort Garrison

Fort Garrison is a bastion of history in Central Maryland. First commissioned around 1693 by Royal Governor Sir Francis Nicholson, Fort Garrison aided in guarding trade routes throughout Maryland. Prior to becoming property of Baltimore County in 1965, this building had been under private ownership for over 100 years.
In addition to guarding trade routes, soldiers were stationed at Fort Garrison in the mid-1700s during the historic French and Indian War. As such, this stone blockhouse had a variety of uses in the past.
In the modern day, Fort Garrison is a bastion of Maryland history. Located in Baltimore County, this fort will forever live on as one of Central Maryland’s most famous historic structures.
Baltimore City – Mount Clare Mansion

The Mount Clare Mansion was constructed around 1756 on the site of the Carroll family plantation. The structure was likely built using slave labor, though paid workers may have also been part of the construction crew.
The original house built at Mount Clare was a one-and-a-half-story house for Charles Carroll’s son, John Henry. John and Dr. Carroll passed away around 1754. After inheriting the plantation, Dr. Carroll’s eldest son, Charles Carroll, Barrister, chose to replace the smaller structure with a Georgian mansion to act as a summer home.
The Mount Clare Mansion is now known as the Mount Clare Museum. Marylanders can visit the site at select times to take a tour of the house to learn more about the mansion, its workers and the inhabitants who once lived there — offering a window into Maryland’s past.
Annapolis – Shiplap House

Constructed around 1715, the Shiplap House served as a tavern and storefront in the 1700s. The name “shiplap” is in reference to the building’s rear siding, which is derived from a shipbuilding technique.
Like other historic buildings in Maryland, the Shiplap House underwent a restoration process over a period of decades in the 1900s, offering greater insight into its construction. Though there is some debate, the Shiplap House is considered by many to be one of the oldest surviving buildings in Annapolis.
Today, the Shiplap House serves as the office for the Historic Annapolis Foundation, a fitting use for a building frozen in time.
Got a tip or photo? Text us at 888-871-NEWS (6397) or email news@thebaynet.com.
Join The BayNet Membership for exclusive perks and zero ads.
Don’t miss a story—sign up for our newsletter!
