Drive 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.
Leonardtown
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.
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.
St. Clement's Island
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.
The 40-acre island is now a state park and is accessible by private boat or by a seasonal water taxi operated by the St. Clement’s Island Museum. There is a sandy beach and picnic area, and seasonal lighthouse tours are available via the museum. If hoping to take a water taxi to the island, be sure to always call ahead (301-769-2222) to confirm water taxi operation and weather conditions. High wind, rough water, rain, or storms and other extenuating circumstances will prevent the water taxi from operating. Rates are $7 per person, which includes children of any age.
If you’ve never been to St. Clement’s Island, this is one stop I highly recommend!
Historic St. Mary's City
Heading back towards Solomons and south towards the tip of the peninsula, you’ll want to stop at Historic St. Mary’s City. Now that you’ve seen the site where the colonists arrived on the Ark and the Dove, you can view the replica Maryland Dove in person. The first replica was built in 1978 and is now in dry dock at an off-site location. In 2019, construction began on a new Maryland Dove in full public view at the Chesapeake Bay Maritime Museum in St. Michaels, MD. At the Historic St. Mary’s City waterfront, visitors can climb onboard Maryland Dove, chat with the ship’s crew, and learn the hardships and benefits of life aboard a trading vessel. Discover how sailors navigated by the stars, what they ate during a long voyage, and how the concepts of colonization affected the land, people, and culture in the region.
Apart from the waterfront, there are many other exhibits to explore, including the reconstructed State House of 1676, the Brick Chapel (ca. 1667), the Woodland Indian Habitat, Godiah Spray Tobacco Plantation, archaeological sites, and more. Your best bet is to spend an afternoon leisurely strolling the exhibits and trails around the property; you won’t want to rush things.
St. Mary's College
Historic St. Mary’s City, or simply ‘Historic,’ as we used to call it in my college days, is located adjacent to St. Mary’s College of Maryland. So, if you visit one, you should definitely save time to do both. Even if you are not an alumnus of the college, you’ll enjoy wandering the beautiful waterfront campus with its brick-lined paths, scenic pond and beach, and the nearby cemetery on the bluffs overlooking the St. Mary’s River (it’s not as creepy as it sounds; in fact, it’s quite lovely). And if you’re in the area, you simply can’t leave without hitting up the Green Door Tavern. Trust me, it’s a St. Mary’s institution.
From the very first time I crossed over the Solomons bridge and every time in the years since that I round that bend and St. Mary’s College first comes into view, it feels like coming home, no matter how long I’ve been away. There are so many more places to explore, but I had to cut myself off eventually. St. Mary’s County is home to some of the most beautiful and peaceful waterfront in the state (IMHO), so if you’re looking for someplace new to visit this summer, definitely put it on your list!
And if coming by boat, check out proptalk.com/chesapeake-bay-marinas and proptalk.com/dock-bars for suggestions on local marinas and waterfront restaurants.
By Kaylie Jasinski
For Vintage Powerboat Enthusiasts:
The Southern Maryland Boat Club hosts vintage race boat exhibitions each summer in St. Mary’s County. At print time, we will have just missed the first event, the Piney Point Rumble on the River June 7-8. So mark your calendars for the Leonardtown Bash on the Bay July 26-27 at Leonardtown Wharf Park! There’s free admission, a food truck on site, and access to the pits and drivers during lunch. Visit southernmarylandboatclub.com for more information.
Fishing Paradise
Enjoy a quiet getaway at Dennis Point Marina and Campground nestled on Carthagena Creek just off the St. Mary’s River. You can camp at one of 118 sites, rent one of their cabins, or for larger groups they have a 3-bedroom house available. The property is incredibly spacious and has plenty of room for your boat and trailer. There is a full marina, as well as a boat ramp, and transient dock. Also on the premises is Capt. Pat’s seafood restaurant which offers excellent crab cakes and fried soft crab. (The food was so good, we ate three meals there!).
In mid-summer, rockfish, speckled trout, and slot red drum can be found in weed beds just a stone's throw from the marina. Casting weedless paddletails under popping corks is a surefire method for targeting these fish. The mouth of the St. Mary’s River where it opens into the Potomac River is just over four miles away. The shoreline around Piney Point also offers good fishing opportunities. There you will also find the Ruddy Duck, another restaurant worth checking out, that is accessible by boat.
Approximately four miles upriver just past St. Mary’s College you’ll find Horseshoe Bend. In the summer of 2024, the Chesapeake Bay Foundation, in partnership with the Maryland DNR and CCA MD, deployed 600 oyster reef balls just off Horseshoe Point. This new habitat is certainly one that anglers should check out! ~Zach Ditmars