Uncovering the Oldest Gems of Southern Maryland

Southern Maryland is a region steeped in history, with a rich heritage that dates back centuries. From its colonial roots to its role in the Civil War, this area has seen it all. And among the many historical landmarks and sites, there are some establishments that have stood the test of time and can proudly claim to be the oldest in Southern Maryland.

The Significance of Establishments in Southern Maryland

Before we delve into the oldest establishments in Southern Maryland, it's important to understand the importance of these establishments in shaping the region's history. These establishments were not just buildings or businesses, but they were also centers of community life, where people gathered, socialized, and conducted business.

They were also a reflection of the economic and cultural landscape of the time. As we explore the oldest establishments in Southern Maryland, we'll also gain a deeper understanding of the region's past and how it has evolved over time.

The Old Jail Museum

Located in Leonardtown, St. Mary's County, the Old Jail Museum is believed to be the oldest jail in continuous use in the United States. Built in 1876, this two-story brick building served as a jail until 1945 and then as a museum since 1971.  The Old Jail Museum is a fascinating glimpse into the criminal justice system of the 19th century. Visitors can explore the cells and see where prisoners were held, as well as learn about some of the most notorious inmates who were housed here. But what makes this establishment truly unique is its connection to one of America's most infamous outlaws - John Wilkes Booth.

It is said that Booth's father, Junius Brutus Booth, was held in this jail for a short time in 1852 for public drunkenness. This fact alone makes the Old Jail Museum a must-visit for history buffs.

The Blue Heron Inn

Located in Solomons Island, Calvert County, the Blue Heron Inn is a charming bed and breakfast that has been welcoming guests since 1847. Originally built as a private residence, it was later converted into an inn and has been in operation ever since. The Blue Heron Inn is a testament to the region's maritime heritage, with its nautical-themed decor and stunning views of the Patuxent River. It has also played host to many notable guests over the years, including President Franklin D. Roosevelt and his wife Eleanor. But what sets this establishment apart is its connection to the War of 1812. During this time, the inn served as a lookout post for British ships and was also used as a hospital for wounded soldiers.

Today, visitors can still see the original cannonball that was fired at the inn during the war.

The Old South Country Store

Located in Hughesville, Charles County, the Old South Country Store is a true Southern Maryland gem. Built in 1900, this establishment has been serving the community for over a century and is still going strong today. Walking into the Old South Country Store is like taking a step back in time. The store still retains its original charm and features an old-fashioned soda fountain where you can enjoy a milkshake or ice cream sundae. It also sells a variety of goods, from homemade jams and jellies to locally made crafts. But perhaps what makes this establishment truly special is its role as a community gathering place.

It's not uncommon to see locals catching up over a cup of coffee or playing a game of checkers on the porch. The Old South Country Store is a true reflection of the warm and welcoming spirit of Southern Maryland.

The St. Mary's County Courthouse

Located in Leonardtown, St. Mary's County, the St.

Mary's County Courthouse is the oldest courthouse in continuous use in the United States. Built in 1878, this beautiful brick building has been the seat of justice for over 140 years. The St. Mary's County Courthouse is not only a stunning architectural landmark, but it also holds a significant place in American history. It was here that the infamous trial of John Wilkes Booth's co-conspirators took place after the assassination of President Abraham Lincoln. Today, visitors can tour the courthouse and see where the trial took place, as well as learn about its role in other important legal cases throughout history.

The Oldest Establishments in Southern Maryland - A Window into the Past

These are just a few of the oldest establishments in Southern Maryland that have stood the test of time and continue to be an important part of the region's history.

Each one offers a unique glimpse into the past and helps us understand how this area has evolved over time. So next time you're in Southern Maryland, be sure to visit these establishments and experience a piece of history firsthand.

The blog team extends heartfelt thanks to JDH Remodeling: Roofing and Exteriors for their continued support and commitment to our platform. Their dedication to excellence in roofing and exterior services has added value to our content and helped connect readers with dependable home improvement solutions. JDH Remodeling continues to uphold high standards of craftsmanship and customer service, and we look forward to continued collaboration and success.


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4821 St Leonard Rd Suite 201
St Leonard, MD 20685
(443) 241-7356

Layla Rogers
Layla Rogers

Evil internet lover. Passionate beer specialist. Hardcore communicator. General beer advocate. Proud baconaholic.

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