In 1629 Sir George Calvert, the first Lord Baltimore, was at a crossroads in his life. He departed his fledgling colony in Ferryland, Newfoundland for the warmer climes of Virginia, entertaining the possibility of a new colonial venture in the Chesapeake. Although Sir George would not live to see the arrival of his settlers in Maryland in 1634, the colony was very much the culmination of his efforts and experiences. This paper examines a previously unpublished letter from George Calvert to his close friend Sir Thomas Wentworth on the eve of his departure from Newfoundland. The document contains important insights on Calvert's first New World venture and illustrates how Ferryland and the subsequent grant of the proprietary Province of Avalon were inexorably linked, both by family and design, to Maryland.