The modeling of genotype × environment interactions (GEI) is important to understand how new crops perform in different environments and management systems. Naked barley (Hordeum vulgare L.) is a type of barley where the hull threshes freely from the grain and can be used for multiple end uses, including food, malt, and animal feed. We examined the performance of a winter naked barley trial grown in organic conditions across three regions and 3 years in northern latitude regions of the United States. We recorded yield, test weight, heading date, plant height, threshability, winter survival, barley stripe rust (Puccinia striiformis f. sp. hordei Westend), barley scald (Rhynchosporium commune Zaffarano, McDonald and Linde sp. nov), and spot blotch (Cochliobolus sativus, anamorph Bipolaris sorokiniana (S. Ito & Kurib.). Barley stripe rust, plant height, heading date, preharvest sprouting, and threshability had high heritability and low GEI. Grain yield, test weight, scald, and winter survival had high GEI and were analyzed using the additive main effect and multiplicative interaction (AMMI) model, genotype plus GEI biplot (GGE), and Finlay–Wilkinson (FW) stability analysis. The environmental patterns explained by the AMMI and GGE models indicated that selection for high GEI traits should occur within target environments and across multiple years within the target environments. Environmental groups were separated by Oregon as the first group and Wisconsin and New York as the second group.