A statistical downscaling approach based on multiple linear-regression is used to investigate the predictability of land surface winds over the Canadian prairies and Ontario. This study's model downscales mid-tropospheric predictors (wind components and speed, temperature, and geopotential height) from reanalysis products to predict historical wind observations at thirty-one airport-based weather surface stations in Canada. The model's performance is assessed as a function of: season; geographic location; averaging timescale of the wind statistics; and wind regime, as defined by how variable the vector wind is relative to its mean amplitude. Despite large differences in predictability characteristics between sites, several systematic results are observed. Consistent with recent studies, a strong anisotropy of predictability for vector quantities is observed, while some components are generally well predicted, others have no predictability. The predictability of mean quantities is greater on shorter averaging timescales. In general, the predictability of the surface wind speeds over the Canadian prairies and Ontario is poor; as is the predictability of sub-averaging timescale variability. These results and the relative predictability of vector and scalar wind quantities are interpreted with theoretically- and empirically-derived wind speed sensitivities to the resolved and unresolved variability in the vector winds. At most sites, and on longer averaging timescales, the scalar wind quantities are found to be highly sensitive to unresolved variability in the vector winds. These results demonstrate limitations to the statistical downscaling of wind speed and suggest that deterministic models which resolve the short-timescale variability may be necessary for successful predictions. / Graduate