Pastures provide substantial habitat for grassland birds of management concern in the Driftless Area of southwestern Wisconsin. The rolling topography in this region is characterized by lowland valleys surrounded by relatively steep and often wooded slopes which are set apart from more expansive treeless uplands. We hypothesized that there would be lower densities of area sensitive grassland passerines in lowland grasslands compared to upland grasslands because of their preference for larger more open grasslands. To test this hypothesis and assess how well pasture area and vegetation structure predicted grassland passerine density compared to upland/lowland status, we conducted point counts of birds in 60 pastures in May–June 1997 and 1998. Upland pastures generally supported greater densities of grassland passerines than lowland pastures. Densities of Savannah sparrow (Passerculus sandwichensis) and bobolink (Dolichonyx oryzivorus) were significantly higher in upland pastures than in lowland pastures. Grasshopper sparrow (Ammodramus savannarum) density was significantly higher on uplands in one of the study years. The density of eastern meadowlark (Sturnella magna), western meadowlark (S. neglecta) and sedge wren (Cistothorus platensis) did not differ significantly between uplands and lowlands. Grassland passerine density was also predicted by pasture size and vegetation structure. Densities of bobolink and grasshopper sparrow were higher in larger pastures. Bobolink and Savannah sparrow occurred on pastures with greater vegetation height-density and less bare ground; bobolink also preferred shallower litter depths. Lowland pastures supported grassland bird species of management concern and should not be neglected. However, we recommend that pasture management for grassland passerines in areas of variable topography favor relatively large upland pastures that will contain higher densities of species of management concern.