Mom holding child at Festival

Five Great Reasons to Visit Leonardtown

Small town charm, artists soul

Mom holding child at Festival

With so much to do so close at hand, it’s no wonder Leonardtown earned its antebellum moniker, “A most convenient place.” Wineries, galleries, history and more make Leonardtown a great getaway just a short hop from Baltimore, Annapolis and Washington, D.C.

Southern Maryland’s Only Arts & Entertainment District
Plein Air Painting in Leonardtown
St. Mary's County

Home to the St. Mary’s Arts Council, art galleries, studios, shops and restaurants, the Leonardtown A&E District packs quite a punch into just 100, walkable acres. So get a glass of Port of Leonardtown wine, chill to the tunes of a local jazz trio and explore this hip oasis in the quiet Southern Maryland countryside. 

SUP & Kayaking from the Leonardtown Wharf
Kayak at Leonardtown Wharf

There’s just nothing like a city on the water, and Leonardtown, nestled on the banks of the Potomac River, will show you why. Meander the new Leonardtown Wharf Park for stirring sunset views or take the plunge and rent a kayak or SUP. You’ll fall in love with the view of Leonardtown from the water at the Wharf.


Explore Amish Country
Amish Quilt Auction
Visit St. Mary's County, Maryland

Hop on your bike and take a quick detour into Leonardtown’s nearby Amish and Mennonite communities. For lovers of traditional crafts, the Amish Quilt Auctions held Saturdays in November are an absolute must. And the traditional craftsmanship of Amish made furniture makes for a functional heirloom that will last generations. And it’s all just minutes from downtown.  

Raise a Glass at the Port of Leonardtown Winery
grape vines and red barn in mist
Port of Leonardtown Winery

Located in the heart of downtown, Port of Leonardtown has quickly become a fixture for the city, but for the East Coast wine community. Combining a welcoming atmosphere with fantastic wines made from locally grown grapes, it’s a great spot to enjoy the day and their gold-medal winning wines. 

Step Out for First Fridays
Maryland flag guitar

Meander historic Town Square, explore used book stores, craft spaces and galleries, or just find an outdoor table for a glass of local wine, a feast of St. Mary’s produce and first rate people watching. Combining a chic artistic aesthetic with Southern Maryland charm, First Fridays in Leonardtown are a perfect night out.