The exacerbation of floods and the extension of droughts, attributed to climate change and human-induced factors, are posing a substantial risk to communities by causing water scarcity. The significance of safeguarding water resources and managing them is increasingly gaining prominence. Snow is an efficient source of water for recharging groundwater compared to rainfall. This is attributed to its gradual melting process and capacity to infiltrate the soil, thereby providing sustenance to the groundwater. Thus, snow drought can be considered a major contributing factor to the issue of water scarcity. The objective of this study was to investigate the evolution of snow drought over the period since 1980, as well as its impact on agricultural drought across the Upper Mississippi River Basin (UMRB). An analysis is conducted for comparison between the spatial estimations of snow drought in the UMRB and two drought indicators, namely the evaporative demand drought index (EDDI) and water deficit amounts. The effects of the El Niño and La Niña phenomena on the UMRB as well as the results of the summer agricultural drought conditions were investigated since 2000. The results point to two important findings: 1) the snow-drought-affected zones show an increasing trend since 1980 and 2) severe snow droughts in the winter (from October to April) of a water year trigger severe agricultural droughts in the summer months of the same water year since 2000. It is seen that monitoring snow droughts is as essential as following rainfall regimes in the planning of water resources, agricultural production, and irrigation methods.