First Landing Wine Trail
Experience the Beauty, the Magic, and the Flavor of the First Landing Wine.
The First Landing Wine Trail pays homage to Maryland's birthplace where settlers first came ashore on St. Clement’s Island in 1634 and established the first settlement in St. Mary’s City.
Come out and visit our state's oldest and one of the most historic areas, and pair it with a new tradition of award winning wines.
About Our Winery
Generations Vineyard is a small family owned and operated vineyard in Leonardtown, Maryland founded in 2012. The vineyard is part of Wheatleys Content Farm...Recent Posts
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Upcoming Events
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About Our Winery
You’ll find us located in the McIntosh Run Park in Leonardtown, Maryland. We feature Local Wines from Local Vines. Our wine tasting is the...Recent Posts
We are working on some awesome content. Check back soon.
Upcoming Events
Live Music & Food Trucks Every Weekend!
12:00am, December 2Read More
About Our Winery
Recent Posts
We are working on some awesome content. Check back soon.
Upcoming Events
There are currently no upcoming events.
