While native grass and shrub restoration is often promoted for bird conservation, evaluations are necessary to understand the effects of habitat change on songbird vital rates and migratory stopover use. We evaluated the effects of native vegetation restoration on the species richness, productivity, and capture rate of breeding and fall migrating songbirds at the Shaker Village of Pleasant Hill, in central Kentucky, USA. From 2009 to 2022, we conducted constant effort mist netting, resulting in 8418 captures of 110 bird species. In 2012–2013, we implemented management in the study area, which began as an old field, to restore native grasses, forbs, and shrubs. Effects on the vital rates of breeding species included higher Spizella pusilla (field sparrow) and Spinus tristis (American goldfinch) productivity post restoration. Restoration of native vegetation also led to significantly higher fall capture rates for pooled cohorts of both long-distance and medium-distance migrants. Our results demonstrate that the restoration and management of native vegetation can enhance stopover habitats for fall migrating songbirds including neotropical migrants and the field sparrow, a common bird in steep decline. We recommend prioritizing areas for native grass and shrub restoration that initially lack structural heterogeneity (a well-developed grass component with diverse forbs and interspersed shrubs).