Maryland 101: Historic St. Mary’s County!

St. Mary’s County is only one and a half hours from Washington, D.C. Yet, it is worlds apart. Dotted with farms that have been handed down generation to generation. This southern tip of Maryland has more to offer than first meets the eye. From a nod to the Amish culture to a strong military history, travel to St. Mary’s County may be just the what the doctor ordered.

brown boat on lake surrounded by green trees during daytime
St. Mary’s County is the southern most point in Maryland off the Western Shore. It is located where the Potomac and Patuxent Rivers meet the Chesapeake Bay.

Historic St. Mary’s City

Have you ever put a wool sweater in the dryer? You know what happens, a perfectly formed miniature of what you had comes out at the end. It seems that we all hold our mistake in our hands and brainstorm which kid will now fit in to the sweater that we once adored. On the flip side, if you took the Williamsburg experience and threw it in the dryer, you would wind up with Historic St. Mary’s City. And that, my friends might be the best mistake you’ve ever made.

This living museum tells the history of the first settlers in the area who arrived in the year 1634. This puts its events just after Jamestown in 1607 and Williamsburg in 1632. Visitors can explore the church, state house, a working farm, a native American settlement and more. Check in with the printer and learn to write with a quill or try your hand at swabbing the deck on a replica ship. Other great historical locations include:

red and white concrete house

Leonardtown Square

Smack dab in the middle of St. Mary’s County is Leonardtown Square. Ringed with restaurants and little shops that truly represent the local character. Over the past few years, the square is experiencing a little bit of a revival. A few standouts are the local speakeasy, a great old school diner, a chocolatier, and for a bit of silly fun, check out the Escape Room. Just off the square, there’s great pizza at the Slice House and an incredible Asian fusion cafe called Jessie’s Kitchen. The bonus? Just a stone’s throw away is the small wharf where you can enjoy the water.

a large bird standing in a body of water

Patuxent Adventure Center

Grab a kayak or a paddle board down at the wharf and make your way through the reeds and waterways which will wind you to the Port of Leonardtown Winery. Win-win. The Port of Leonardtown is among four wineries in the county and all contribute to the Sotterley Plantation Wine Fest, a local favorite.

For more details on anything we’ve mentioned, including addresses, directions, and hours of operation, check out Visit St. Mary’s County.

people kayaking on river

Pax River Aviation Museum

A little know fact: Patuxent River Naval Air Station is home to Test Pilot School where most every astronaut cut their teeth on advanced aviation. This huge base at the point where the Patuxent and Potomac Rivers meet is page one in the Space Race story.

The base has a great museum that explains how Pax River played this important role in promoting naval aviation through the years. The small but mighty building is perfect for military junkies who like to peruse the plane park to get up close and personal with aircraft and give one of the simulators a go. Easy to manage and lots of fun, it’s will worth the visit.

Get Your Shop On!

Southern Maryland is just starting to find its identity in the tourism industry. A big part of that is realizing the local treasures that appeal to visitors. To that, lots of little shops have started popping up that speak to that local charm.

Old Sheppard’s Field Market

For a sampling of tons of local vendors ranging from metalwork to organic meat, step in to this fun gaggle of booths at the old market. Browse and shop away then head toward the back to the Brugarten for a drink and relax in the fun atmosphere.

green and red apples in brown wooden bucket

The Vintage Source

If it’s the third Saturday of the month, locals will tell you that The Vintage Source is the place to find all of those hidden gems serious shoppers look for. From antique dressers to vintage glassware, the stock changes and the finds are innumerable. Other local shops include: