Across the Midwest, farmers, researchers, policy makers and communities are confronting increasing groundwater contamination due to agricultural practices, particularly the use of synthetic nitrogen fertilizer, coupled with the challenge of employing these practices to continue growing profitable crops. Additionally, not only are the impacts of agricultural practices felt at the local level-often in the form of agricultural runoff, unsafe drinking water, soil erosion, and decreased stream and lake levels-but also nationally. As agricultural runoff travels downstream to the Gulf of Mexico, excess nutrients have resulted in dead zones. It is likely that ongoing and future climate change across the Midwest will exacerbate current struggles and may leave many fields more vulnerable to nitrate leaching. Moving forward, to ensure safe drinking water and restore and protect ecosystem services, nitrogen management strategies need to be improved and implemented. The Wisconsin Central Sands (WCS) faces many of the challenges felt by communities across the Midwest when managing agricultural land with growing water quality contamination. The WCS region serves as a case study in improving nitrogen management for groundwater quality. To better identify pathways to improved groundwater quality, we incorporated on-farm research related to drivers of water quality variability, observations of soil-plant-environment interactions, agroecosystem modeling, and farmer surveys. In chapter one, we evaluated/quantified the spatiotemporal variability of nitrate concentrations in irrigation water across the WCS region. Additionally, we analyzed the influence of well depth, well casing diameter, nitrogen application rate, year and week of sampling event on nitrate concentration in irrigation water. We found that nitrate levels varied more across space than time, that nitrogen application rate was the most significant predictor of nitrate concentration, and that on average, nitrate levels in irrigation water across the WCS are 19.0 mg/L, or nearly twice the threshold for safe drinking water set by the EPA. In chapter two, we measured leaf level photosynthesis and calculated key photosynthetic parameters for two cultivars of potato grown under four nitrogen application rates. We found that nitrogen application rate (season total N), days after emergence (DAE), and temperature were significant predictors of Vcmax (maximum rate of carboxylation). We also found that at the highest level of nitrogen application (403.5 kg N/ha), both N content (%) and Vcmax declined relative to a nitrogen application rate of 336.3 kg N/ha. In chapter three, we modeled the impact of nitrogen best management practices (BMPs) with varied N rates on irrigated corn yield and nitrate leaching. To better understand the effectiveness and tradeoffs of BMPs considering increased weather variability, we used cluster analysis to group similar weather years. We found that nitrate leaching could be reduced through the use of BMPs (20%) and reduced nitrogen application rates (40%), but there was little room for mitigation during years experiencing wetter than average growing seasons. Additionally, nitrate concentration in the groundwater never reached safe/healthy levels (below 10 mg/L) in our simulations. In chapter four, we surveyed farmers on their current use of nitrogen BMPs, levels of concern towards environmental and economic challenges, as well as barriers to implementing certain BMPs. Our findings highlight that growers feel the greatest level of concern for the cost of government regulation and ineffective government policies, and 100% of respondents felt at least a little concerned about groundwater quality. While the BMP of split application was widely adopted (69%), growers perceived lack of information as a substantial barrier to adopting the practice of crediting nitrate in irrigation water.