The addition of planted grasslands (i.e., fields that have been planted with exotic grass and forb species) to the North American landscape has been beneficial for the conservation of many species, but not necessarily for species that show a preference for native grasslands. Under what conditions these planted fields are attractive to native grassland specialists is unclear. Sprague's Pipit (Anthus spragueii) is a native grassland specialist, but it breeds in planted grasslands in some parts of its range. We conducted a comparative study of territory and nest use by Sprague's Pipits in native pastures and planted hay fields from 2006 to 2008. In planted hay fields, territories were characterized by vegetation height of 25 cm and litter depth of <1.5 cm; in native pastures, the birds used territories with 15% bare ground and <1.5 cm litter depth. Nests in both habitats were located in areas with vegetation height of 25–30 cm, whereas random areas had either taller or shorter vegetation. Territories were associated with different vegetation characteristics in both habitats. Sprague's Pipits used the same nest characteristics in both habitat types, which suggests that they found areas within planted grasslands that closely resembled areas that they might use for nesting in native grasslands. Planted fields with a low amount of alfalfa and suitable vegetation height (20–30 cm) should be attractive to breeding Sprague's Pipits.