In the words of the psalmist, “wine gladdens the heart of people” (104:15), and viticulture—the art and practice of growing grape vines—was of central importance in the ancient Near East. It should then come to no surprise that viticulture in the eschaton would also be important. This study looks at three of the most prominent instances of eschatological viticulture in early Judaism and Christianity, namely 1 Enoch 10.19, 2 Baruch 29.5, and Papias in Irenaeus, Adv. haer. 5.33.3, paying particular attention to their tradition histories and intertextual relationships. All three of these texts imagine that the grape vine will be fantastically productive in God’s renewed creation, but they develop this image in different ways based on different biblical texts. First Enoch uses the trope in conjunction with its use of the account of Noah’s renewal of the earth after the Flood in Gen 9. Second Baruch uses it to present an eschatological banquet feasting upon the primordial beasts of Leviathan and Behemoth in a return to the paradise of Gen 2. Papias, in contrast, applies the trope to the Blessing of Isaac in Gen 27. Though these accounts are all different in their application, they all feature the same sensibility: what gladdens the heart in this world will also gladden the heart in the age to come.