The presented work deals with the spread of viticulture and fruit farming in the Middle Ages in the Samtskhe-Javakheti region in Georgia. The current state of the farming sectors mentioned and those pivotal moments in Georgian history that had an influence on agriculture are also considered in the article. The changes that determined the viticulture geography from the second part of the 16th century up to the present day are also discussed. The study is mainly based on the census document created in 1574. The article represents the geographic distribution patterns of vineyards and orchards, as well as wine production capacity and the fruit harvest. Retrospective mapping made it possible to restore the distribution of farms and gardens of the mentioned period and to analyse the importance of viticulture and fruit farming in the 16th century. The maps represented show spatial patterns of vineyards, gardens, and main terroirs.