Terrestrial proxies of wind direction spanning the last deglaciation suggest easterly winds were present near the Laurentide Ice Sheet margin in the North American midcontinent. However, the existence and spatial extent of such easterly winds have not been investigated with transient paleoclimate model simulations, which could provide improved dynamical context for interpreting the causes of these winds. Here we assess near-surface winds near the retreating southern Laurentide Ice Sheet margin using iTRACE, a transient simulation of deglacial climate from 20–11 ka. Near the south-central margin, simulated near-surface winds are northeasterly to easterly through the deglaciation, due to katabatic flow off the ice sheet and anticyclonic circulation. As the ice sheet retreats and the Laurentide High moves northeastward and weakens, near-surface northeasterly winds weaken. Meltwater fluxes also influence temperature and sea level pressure over the North Atlantic, leading to easterly wind anomalies over eastern to midwestern North America. The agreement between proxy and model wind directions is promising, although simulated easterly to northeasterly winds extend too far south in iTRACE relative to the proxy data. Agreement is also strongest in winter, spring, and fall, suggesting these may have been seasons with greater aeolian activity.