With perfect timing, Preservation Maryland supporters Diane and Jeff Caslow traveled to St. Mary’s County on this March coinciding with Maryland Day and checking off the eighteenth county on their twenty-four month quest to visit all of Maryland counties.


Of all the planning we do for our monthly trips, it was actually a coincidence that we chose St. Mary’s for the month of March as many Marylanders know Maryland Day is celebrated on March 25 in recognition of the landing of Maryland’s first colonists in 1634. We thought it would be fun to see some of the connections to the past, and of course, some unexpected finds along the way.

Charlotte Hall in St. Mary's County, 2018.

Charlotte Hall in St. Mary’s County, 2018.

Charlotte Hall

First stop is a historic marker that I have driven by many times. This one leads us to one of the churches on the St. Mary’s Historic and Religious Sites guide managed by St. Mary’s County Division of Tourism. Dent Chapel is on the grounds of the Charlotte Hall’s Veterans Home. Charlotte Hall School was established in 1774 and in 1852 became known as Charlotte Hall Academy, surviving for over 200 years. When it closed, most of the buildings were demolished to make way for the Charlotte Hall’s Veterans Home. However, in finding Dent Chapel, built in 1883, right across the street is one of the only remaining buildings of Charlotte Hall Academy, The White House, built in 1803.


Next stop was supposed to be St. Clement’s Island, but I needed coffee first and read that there was a place to get a Southern Maryland delicacy, a stuffed ham sandwich, at a little deli in Chaptico. It also happens that one of the oldest churches on the Division of Tourism’s list, built in 1736, is also in Chaptico. Christ Episcopal Church’s construction was supervised by Philip Key, vestryman, the grandfather of Francis Scott Key. The cemetery includes a vault for the Key family.

Painting of Francis Scott Key. Image from Mount Vernon.

Painting of Francis Scott Key. Image from Mount Vernon.

St. Clement’s Island

On to St. Clement’s Island for a glimpse of what must have been a sight after four months at sea from the Isle of Wight in England to the shores of a new world.  “The island was named in honor of Pope Saint Clement I, patron of mariners. It was the site of the first Roman Catholic Mass celebrated in the British-American colonies, said by Jesuit Father Andrew White, and widely believed that the Mass took place on the day of the landing.” The island ferry is not yet open for the season and the St. Clement’s Island Museum on the mainland is not open until the afternoon. We walk around a bit and simply contemplate the history made here 384 years ago. We saw a sign for a Southern Maryland Oyster Trail and made a note to learn more about it later.

St. George’s Island and St. Jerome Creek

Our next stop took us way off the beaten path, and I am glad it did…

We drove to the very end of St. George’s Island and spied an interesting sign, “Fins and Claws – A Maritime Presentation by Capt. Jack.”  We drove in and out came Jack Russell, who was in the midst of preparing an oyster roast for twenty people that afternoon. He is pretty well known in the area, especially for his skipjack, the Dee of St. Mary’s, as a waterman and as an educator through what was the Chesapeake Bay Field Lab. You could tell that he is passionate about his oysters and sharing his knowledge. We were rapt students as he gave us a deeper understanding of life on the water, a lesson in the best way to shuck an oyster, and a taste of a fresh oyster. He said you could tell the age of the oyster like tree rings, showing us one about ten years old and as big as my hand.

A stop for lunch, more oysters and fresh caught rockfish, and then we are in search of a modern oysterman. We headed to St. Jerome’s Creek to find an oyster farm, True Chesapeake Oyster Co., started in 2013 by Patrick Hudson.

St. Mary’s City

We drove past Woodlawn Manor, not realizing its history as one of the oldest manor houses, built in 1634 and Slack Winery, not yet open for the season. We will be back to visit both!

So on to St. Mary’s City. It was Maryland’s first colonial settlement, and is now a reconstruction of the original colonial settlement, living history areas, museums and the campus of St. Mary’s College of Maryland. As we are out of season, much of Historic St. Mary’s City is not open, but we can still explore it a bit, including the replica of the The Dove. It was one of two ships, along with The Ark, which made up the first expedition from England to the Province of Maryland. One of the interpretive history signs actually brings us back to Jack Russell as it tells the story of his skipjack, the Dee of St. Mary’s. From the vantage point of the Trinity Episcopal Church we watch the modern-day sailors enjoying a Sunday afternoon.

Vernacular commercial building in Leonardtown, MD, 2018.

Vernacular commercial building in Leonardtown, MD, 2018.


We took a walking tour of Leonardtown and found an interesting mix of buildings around the town square, including my favorite kind of adaptive reuse — a chocolatier, Heritage Chocolates. The town was officially established in 1708, and is the county seat, but records show that county court business was conducted as early at 1654. We took a walk down to the Leonardtown Wharf Park, which was once a busy steamboat landing.

Sotterley Plantation. Photo from the Maryland Historical Trust.

Sotterley Plantation. Photo from the Maryland Historical Trust.

Sotterley Plantation

Our final stop was Sotterley Plantation. It was declared a National Historic Landmark in 2000, due, in part, to the extremely rare surviving elements of the main house’s oldest phase, around 1717. As it is closed for the season, we put some money in the donation box and walk around the grounds to enjoy the end of our day…

Next month our journey takes us to Carroll County.