This research examines the breeding habitat preferences of grassland birds at Fort Drum, Jefferson County, New York during the 2011 and 2012 breeding seasons. In the past, Fort Drum and surrounding areas in Jefferson County have supported large numbers of obligate grassland breeding birds. However, results from this study, when combined with data from past studies of grassland birds at Fort Drum, suggest that habitat specialists such as the sedge wren (Cistothorus platensis) and Henslow’s sparrow (Ammodramus henslowii) have been continually declining. Reasons for the decline are most likely related to a decrease in agriculture resulting in habitat loss due to succession and a shift in agricultural practices. Habitat models suggest that obligate grassland breeding birds (OGBB) prefer increased graminoid cover and shorter less dense vegetation. Differences in the models between years suggest that the predictive power of modeling is limited and that models should be used only as management guidelines.