North American grassland birds have widely declined over the past 50 years, largely due to anthropogenic-driven loss of native prairie habitat. In response to these declines, many conservation programs have been implemented to help secure wildlife habitat on private and public lands. The Grasslands Coalition is one such initiative established to advance the conservation of grassland birds in Missouri. The Missouri Department of Conservation conducted annual point count surveys for comparison of grassland bird relative abundance between focal grassland areas and nearby paired (i.e., containing no targeted management) sites. We analyzed 17 years of point count data with a generalized linear mixed model in a Bayesian framework to estimate relative abundance and trends across focal or paired sites for nine bird species of management interest that rely on grasslands: barn swallow (Hirundo rustica), brown-headed cowbird (Molothrus ater), dickcissel (Spiza americana), eastern meadowlark (Sturnella magna), grasshopper sparrow (Ammodramus savannarum), Henslow's sparrow (A. henslowii), horned lark (Eremophila alpestris), northern bobwhite (Colinus virginianus), and red-winged blackbird (Agelaius phoeniceus). Relative abundance of all species except eastern meadowlarks declined regionally. Relative abundance of barn swallows, brown-headed cowbirds, dickcissels, eastern meadowlarks, Henslow's sparrows, and northern bobwhites was higher in focal than paired sites, though relative abundance trends were only improved in focal vs. paired areas for dickcissels and Henslow's sparrows. Relative abundance increased with increasing grassland cover at the local (250-m radius) scale for all species except horned larks and red-winged blackbirds and at the landscape (2,500-m radius) scale for all species except dickcissels, eastern meadowlarks, and northern bobwhites. Our results suggest focal areas contained greater relative abundances of several grassland species of concern, likely due to increased availability of grassland habitat at local and landscape scales. Further efforts to decrease landscape-scale fragmentation and improve habitat quality may be needed to achieve conservation goals.