Migratory birds time their migration based on cues that signal resource availability for reproduction. However, with climate change, the timing of seasonal events may shift, potentially inhibiting the ability of some species to use them as accurate cues for migration.  We studied the relationship between phenological shifts and reproduction by long- and short-distance migratory songbirds—Bobolinks (Dolichonyx oryzivorus) and Savannah Sparrows (Passerculus sandwichensis). Our study population breeds in hayfields and pastures in Vermont, USA, where farmers are also changing management activities in response to climate change. From 2002-2019 we monitored nest initiation dates to quantify correlations with environmental factors and the timing of nest initiation. We collected historical and projected precipitation and temperature data for the breeding grounds, and their respective wintering and stopover sites, the North Atlantic Oscillation (NAO) and the El Niño Southern Oscillation (ENSO). We predicted that winter conditions experienced by the short-distance migrant, the Savannah Sparrow, but not the long-distance migrant, the Bobolink, would explain the timing and success of nesting, however that this timing would be misaligned with changes in agricultural practices by hay farmers.  Nest initiation dates did not show significant directional change for either species, but did vary among years. Interannual variation in Savannah Sparrow nest initiation dates was best explained by the interaction between precipitation on the breeding grounds and average wintering site (Wilmington, North Carolina). For Bobolinks, interannual variation in nest initiation dates was best explained by the interaction between breeding ground precipitation and average temperature in their fall stopover site (Barquisimieto, Venezuela). However, first haying dates in Vermont advanced by ~10 days over 18 years. These results suggest that the conflict between the timing of hay harvests and grassland songbird reproduction will increase, further threatening population processes for these species, as early harvests notably decrease annual productivity.