Leonardtown
(Sample Route from the Field Guide)
Southern Maryland’s Historic Coastal Gateway
Leonardtown offers a slower-paced entry into Maryland’s rural wine landscape. Located in St. Mary’s County near the Chesapeake Bay, the town blends colonial history, waterfront proximity, and agricultural continuity. From here, visitors can access estate wineries shaped by coastal climate, open farmland, and Southern Maryland tradition.
Historic Background
Founded in the 17th century, Leonardtown sits within St. Mary’s County — the site of Maryland’s first capital and one of the earliest experiments in religious tolerance in colonial America. The region’s early settlement along the Chesapeake Bay established a lasting agricultural and waterfront tradition. That continuity of farmland and open space now supports a small but distinctive wine presence shaped by coastal climate and Southern Maryland’s rural character.
What To See
St. Mary’s City Historic District
Leonardtown Wharf & Waterfront Park
Tudor Hall
Where To Eat
The Front Porch
Olde Town Pub
Botanic Café
Notable Wineries Within 10–30 Minutes
Port of Leonardtown Winery
Known for: Community-supported winery highlighting Southern Maryland fruit and regional blends
Tasting style: Traditional tasting room in downtown Leonardtown
Food: Food Trucks available most weekends
Children: Family-friendly outdoor areas
Pets: Permitted outdoors
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Xella Winery and Vineyard
Known for: Community-supported winery highlighting Southern Maryland fruit and regional blends
Tasting style: Traditional tasting room in downtown Leonardtown
Food: Light snacks available
Children: Family-friendly outdoor areas
Pets: Permitted outdoors
Additional Wineries in the Area
Visitors with additional time may also wish to explore several other wineries located within driving distance of Annapolis.
Corteau Vineyards
Trueman Vineyards and Winery
These wineries can easily be incorporated into extended visits to the region.
Winery hours and reservation policies may vary.
Distance From Washington, DC
Approximately 60–90 minutes from central Washington, DC depending on traffic.
Nearby wineries are generally 10–20 minutes from downtown Leonardtown, making the town an efficient anchor for exploring Southern Maryland’s rural and coastal wine landscape.
This route is just one part of the full system.
Inside the Field Guide, you’ll find many more towns, regions, and carefully designed winery routes across Virginia and Maryland—each built for flow, timing, and experience.
A Structured Approach to Wine Travel
This overview introduces the landscape, but it only scratches the surface of what the region offers.
The complete Wine Country Field Guide expands each destination into a fully designed experience — including curated winery sequences, drive-time optimization, seasonal strategy, and deeper regional context that allows you to move through wine country with clarity and intention.