A Trip Through 3 Centuries in 3 Days through 3 Counties

Calvert, Charles and St. Mary’s Counties
A Trip Through 3 Centuries in 3 Days through 3 Counties

Discover Southern Maryland’s unique past – richly preserved in its numerous historic sites, dynamic museums and rural byways.


Arrive at the Chesapeake Railway Museum in Calvert County to experience life in the early 1900s and the Chesapeake Beach Railway Co. & Amusement Park history detailed in photos and artifacts in the Railway’s only remaining station. Learn the role the Chesapeake Bay environment had in shaping the cultures of Bayside communities, from prehistoric to present times, at the Bay History Museum. Before you leave, take off your shoes and wade into the waters of the Chesapeake Bay at North Beach Public Beach or stroll along the boardwalk and wander into eclectic shops and enjoy lunch at one of the restaurants serving mouthwatering seafood delicacies in this quaint seaside town. Traveling south to see the northernmost natural range of bald cypress trees in the United States at Battle Creek Cypress Swamp Sanctuary. Then ESCAPE TO SOLOMONS ISLAND! Visit the Calvert Marine Museum, which traces the rich maritime history of life found in the Chesapeake Bay. Climb up through the hatch of the Drum Point Lighthouse, constructed in 1883. Beautifully restored, complete with furnishings of the era, it has become the waterfront’s main attraction. Tour the Joseph C. Lore & Sons Oyster House, a restored seafood-packing house that flourished during the boom & decline of the region’s commercial seafood industries. Take a short cruise around the harbor on the historic “bugeye” boat, the Wm. B. Tennison and build up an appetite for dinner. After checking into a local hotel, have dinner at any number of waterside restaurants.


Take a drive over the scenic Thomas Johnson Bridge to St. Mary’s County and travel south to Historic St. Mary’s City, the first permanent settlement in Maryland and Maryland’s first capital. The “city” is now one of the nation’s premier outdoor history museums and archeological parks. While there, get into the spirit of early colonial life with a visit to the Godiah Spray Plantation and the Maryland Dove, a working replica of the square rigged schooner that carried the first colonists from England. Head to Lexington Park where you’ll find manylunch choices, then visit the Patuxent River Naval Air Museum, one of the few official Navy museums. Explore the outdoor air park and test your mettle in a navy flight trainer. Travel a few miles north and several centuries back in time to Sotterley Plantation along the Patuxent River. Tour the rambling manor house and the colorful gardens. It’s just a few miles to Leonardtown for late afternoon shopping in the town’s shops and galleries, wine tasting at the Port of Leonardtown Winery and dinner at one of town’s numerous dining spots. After dinner, stroll the town’s waterfront park along Breton Bay. Spend the night at Leonardtown’s in-town hotel or chose lodging at one of the county’s B&Bs or hotels.


Travel north to the Dr. Samuel A. Mudd House in Charles County. This early Victorian farmhouse was once home of Dr. Mudd, the physician who treated the broken leg of John Wilkes Booth, the assassin of President Abraham Lincoln. This site is included on Maryland’s Civil War Trail project entitled, “John Wilkes Booth: Escape of an Assassin. While on the way to the museum, you will travel some of the escape route, passing by the old Bryantown Tavern where Booth and other Confederate sympathizers met to discuss their plans and St. Mary’s Catholic Church, where Dr. Mudd is buried. Lunch at The Crossing at Casey Jones Restaurant or the Royal Tea Room in LaPlata. Travel west to the Thomas Stone National Historic Site for a visit to Harberdeventure, the plantation home of Thomas Stone, one of Maryland’s four signers of the Declaration of Independence. Both Stone and his wife are buried here. This historic site is managed by the National Park Service and includes a Visitors Center that features exhibits and a gift shop. Continue west to the Historic District of Port Tobacco, once Maryland’s second largest seaport and listed on early World Maps. Originally the site of the Indian Village of Potopaco, Port Tobacco was the first county seat until it was moved to LaPlata in 1895. At the Port Tobacco Courthouse (open seasonally), costumed docents tell the story of this historic area from 1620 to the present. The Port Tobacco area was also home to several Confederate sympathizers during the Civil War. End your visit to the Southern Maryland area by catching a minor league baseball game at the new Regency Furniture Stadium, home of the Atlantic League’s Maryland Blue Crabs, or enjoy a Southern Maryland dining experience in Popes Creek or further down the road on Cobb Island at any one of our waterfront restaurants. Relax by the water while feasting on hot steamed crabs and shrimp, local oysters on the half shell or the fresh catch of the day!

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