The first licensed winery on the Eastern Shore of Maryland, Little Ashby Vineyards, is located on the banks of the Miles River in historic Talbot County, near the quaint colonial towns of Easton and St. Michaels. The winery can be reached by boat as well as by car or bicycle. Its elevated riverbank position gives the vineyards their own distinct microclimate, cooled by river breezes on hot summer nights and moderated by the warmer water temperature during the winter.

The first vines, French vinifera, grafted onto American root stock, were planted in 1994. The winery was built in 1998, and commercial production began in the year 2000. Grapes cultivated at San Sano Estate and Cottingham Farm, nearby vineyards located on tributaries of the Miles River, are added to Little Ashby's own grape harvest to produce merlot, pinot noir, chardonnay and a light red "spring wine” blended from four varieties of grapes.

Little Ashby's owners, winemaker Warren  Rich and his wife Lynne, live on the property with their labrador retrievers, Chester and Teddy Bear, and their labradoodle, "Lola", whose portraits grace the labels of the wines.