Observations made by Earth-based radar telescopes and the MErcury Surface, Space ENvironment, GEochemistry, and Ranging (MESSENGER) spacecraft provided compelling evidence for water ice in Mercury's polar craters. In our investigation, we constructed higher-resolution (125 m pixel−1) digital elevation models (DEMs) for four of the largest northernmost craters, Kandinsky, Tolkien, Chesterton, and Tryggvadóttir. The DEMs were leveraged to model solar illumination and the thermal environment, products that were used to identify permanently shadowed regions and simulate surface temperatures. From these models, we predicted the regions of surface stability for ice and volatile organic compounds. These predictions were then compared against the Arecibo radar, Mercury Laser Altimeter (MLA), and Mercury Dual Imaging System (MDIS) data. Our radar analysis shows that areas of high radar backscatter are correlated with areas predicted to host surface ice. Additionally, we identify radar backscatter heterogeneities within the deposits that could be associated with variations in ice purity, mantling of the ice, or ice abundances. The MDIS analysis did not reveal conclusive evidence for ice or volatiles at the surface, while MLA results support the presence of water ice at the surface in these craters. However, evidence for boundaries between the surface ice and low-reflectance volatile organic compounds, as suggested could be present by our models, was inconclusive owing to the limited MESSENGER data in these regions. BepiColombo’s upcoming orbital mission at Mercury has the opportunity to obtain new measurements of these high-latitude craters and test our predictions for the distribution of surface volatiles in these environments.