Vineyards, Wineries, and Distilleries in Kent County Maryland

The Upper Eastern Shore (including Kent County) is one of the fastest growing grape producing regions in the state of Maryland. Kent County has a number of vineyards and currently one winery. Traveling the Chesapeake Wine Trail is an excellent way to explore these wineries and the beauty of the Upper Eastern Shore.


Crow Vineyard and Winery

12441 Vansants Corner Rd.
Kennedyville, MD 21645
Tel: 302-304-0551


Bad Alfred's Distilling

323 High Street
Chestertown, MD 21620
Tel: 443-282-0163

The Cassinelli distillery and wine bar is located at 323 High Street in Chestertown and is open Thursday through Monday.  Visitors can watch as distilled products, including vodka, gin and brandy, are made and taste them from directly from the stills.

Cassinelli Distillery Bottles



Experience Chesapeake Wine Country

Experience Chesapeake Wine Country promotes the Chesapeake Wine Trail and the growing wine country on Maryland's Eastern Shore to locals and visitors. The site discusses the reputation and availability of the area's local wines.

Chesapeake Wine Trail

Whether you are on your way to the beach or just taking a drive to admire the beautiful Bay, the Chesapeake Wine Trail will lead you through one of the most scenic and charming parts of the state. East of the Chesapeake Bay, Maryland’s Eastern Shore is abundant with seafood, beaches, wildlife and history, and now a beautiful—and delicious—wine trail.