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A Walkable Weekend in Leonardtown

A Walkable Weekend in Leonardtown

Looking for a weekend escape? Plan a visit to charming Leonardtown in Southern Maryland, where you can park your car and spend the weekend exploring on foot. Leonardtown is only an hour and a half away from Washington D.C., and two hours from Baltimore. 

Arrive on the first Friday of the month for an extra-special St. Mary’s experience! 


Set your GPS for The Inn at Leonardtown—this boutique hotel in the heart of Leonardtown will serve as your home base for the weekend. Start the morning with fresh coffee and pastries at Kneaded Bakery or grab made-to-order donuts at Flour Donuts and Bakery.

Learn the story of Benjamin Hance at the Old Jail Museum, a National Park Service Underground Railroad Network to Freedom site and home to the Leonardtown Visitor Center. Head outside to the famous Moll Dyer Rock. Do you believe this local legend?

Photo Credit: Visit St. Mary’s, Maryland

Soak up the charm of the town square while dining al fresco at SweetbayEnjoy a laid-back shopping experience along the town square. Pop into New View FiberWorks, a working studio and boutique offering a variety of artisanal, women-made goods. Turn the corner to grab an armful of treasures from Fenwick Street Books and find the artwork your home is missing at North End Gallery and St. Mary’s Arts Council Gallery & Gift Shop. Or, lean into your creative side and make your own art at The Yellow Line or Board & Brush. Walk just a few blocks from the town square to Shepherd’s Old Field Market and browse the goods of over 90 small businesses all under one roof!

Brudergarten Beer Garden at Shepherd’s Old Field Market, Leonardtown, Maryland. Photo Credit: Visit St. Mary’s, Maryland

Unwind from your day of walking with a glass of wine at Antoinette’s Garden, or keep the party going at Olde Town Pub, The Rex, or Brüdergarten. If you’re visiting in the summer months, be sure to take a sunset cruise around Breton Bay. Cruises depart from Leonardtown Wharf.


Ease into the day with brunch at The Front Porch or Social Coffeehouse and Cocktail Bar and pose for pictures in front of the murals in Leonardtown Alley.

Outside patio of a coffee shop with many patrons sitting at tables
Photo Credit: courtesy of Visit St. Mary’s MD

Rent kayaks or SUPs at Leonardtown Wharf Park and get out on the waters of Breton Bay. Try every flavor of New York-style pizza at The Slice House—locals say it’s the best pizza around! End the weekend on a sweet note with a scoop (or two!) of hand-churned ice cream from The Salted Scoop. Bring a taste of St. Mary’s home with a box of freshly-made chocolates from Heritage Chocolates.


Lush forests, abundant waterways, significant historical sites, and charming small towns await you in St. Mary’s County. Whether you’re relaxing by the waterside, perusing shops, galleries & museums, dining on fresh seafood, or adventuring in the outdoors, you’re sure to find your version of paradise in Maryland’s Original Destination! 


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