See the Bay
By Kaylie Jasinski
D
rive about an hour and a half south from Annapolis and you will hit the tip of St. Mary’s County, MD, home to my alma mater, St. Mary’s College of Maryland. Prior to attending college there, I can’t say I spent too much time in Southern Maryland, but now it will always be a little piece of home. Whether visiting by boat or car, there are miles of shoreline, historical sights, and seafood galore to satisfy any Bay lover. When driving south, you’ll know you’ve reached your destination upon crossing over the (rather steep) Governor Thomas Johnson Bridge aka the Solomons Island bridge. There are so many places to explore, so we’ll try to highlight just a few ‘must-see’ spots. For more ideas, head to visitstmarysmd.com.
About 20 minutes by car from Solomons Island you’ll reach Leonardtown, which received its moniker “a most convenient place” back in the early 18th century. The county’s courthouse, hospital, and governmental center are located here. Shops, galleries, and restaurants are located around the quaint town square and along Fenwick Street and Route 5. Some notable historical sites include Tudor Hall, built in 1744 and once the home of Phillip Key (uncle of Francis Scott Key, author of the “Star Spangled Banner”) and the Old Jail Museum, built in 1876. You’ll also want to visit Port of Leonardtown Winery, home to one of the only cooperative wineries in the country (the Southern Maryland Winegrowers Cooperative), and Fenwick Street Used Books and Music (a must for me every time I’m in town). For a list of more shops and dining options, click to the business directory at visitstmarysmd.com. Year-round, every First Friday of the month, historic Leonardtown’s art galleries, restaurants, cafés, gift shops, antique shops, and bookstores open their doors to showcase local artists and/or serve specials at their establishments. Starting with the month of May each year, Leonardtown First Fridays are extended to Leonardtown First Friday All Weekend Events and continue through October. Find dates and event themes at visitleonardtownmd.com/ firstfridays.
32 June 2025 PropTalk.com
##Courtesy Leonardtown Wharf
During the summer months, visitors can ride the free Leonardtown Trolley to easily get around town; simply hop on and off at any of the trolley stops as you explore. Taking a short trip down the hill from Leonardtown Square along Washington Street will lead you to the Leonardtown Wharf, a picturesque waterfront with a spectacular view of Breton Bay. There you will find a playground, restrooms, boat slips, and a floating dock. Visitors can also stroll along the boardwalk or relax on park benches alongside the water. Free boat tie-ups, canoe/kayak launch, and kayak/ SUP rentals are available; no overnight boat facilities. Not far from town is Newtowne Neck State Park, a 776-acre property surrounded by Breton Bay, the Potomac River, and St. Clement’s Bay. It features woodlands, wetlands, and agricultural fields, making it a prime spot for biking, walking, hunting,
birding, and fishing. Captain John Smith explored the waters surrounding the property in 1608, and Newtowne was the first settlement in the Maryland province after St. Mary’s City. Another short drive away is the St. Clement’s Island Museum in Coltons Point, MD, the gateway to St. Clement’s Island and the birthplace of Maryland. On March 25, 1634, the first English settlers under the Baltimore proprietorship sailed to St. Clement’s Island on the Ark and the Dove. This Potomac River island features a 40-foot cross commemorating the founding as well as the reconstructed Blackistone Lighthouse. The original lighthouse was constructed in 1851, burned in 1856, and has since been rebuilt by the community whose forbears’ lives once centered upon the light.