<p>Investigating the spatiotemporal changes in winter wheat cultivation across the Huang-Huai-Hai Plain (3HP) of China is essential for maintaining regional food security and mitigating climate change challenges. Previous studies have primarily focused on forecasting potential planting areas based on meteorological data, while comprehensive analyses of long-term changes in actual cultivated areas remain limited. To address this gap, this study explores the spatial and temporal dynamics of winter wheat planting using satellite-derived datasets, incorporating the Mann–Kendall test, Sen’s slope estimator, Moran’s I index, hot spot analysis, and standard deviational ellipse (SDE) techniques. The findings reveal that over the past two decades, winter wheat cultivation in 3HP has exhibited a high degree of continuity, with 65.01% of pixels experiencing more than a decade of uninterrupted planting, and nearly half of the cultivated areas displaying a significant increasing trend. While the spatial clustering of wheat cultivation has shown little change over time, notable shifts in the centroid of planting activity have been observed, with a 30.86&#xa0;km southeastward displacement, mainly driven by temperature, precipitation, irrigation, and urbanization. These insights contribute to refining agricultural policies for winter wheat, supporting adaptive strategies in response to climate change while safeguarding food security.</p>