Anthropogenic alterations to landscapes have increased as the human population continues to rise, leading to detrimental changes in natural habitats. Ecological restoration assists in recovery by altering habitats to improve conditions and foster biodiversity. We examined land cover changes over time within a complex, dynamic region in the Midwest to assess the long-term effects of conservation. We used Landsat 8 bands for a 15-class land cover map of Oak Openings Region using supervised classification. We validated our map and achieved an overall accuracy of 71.2% from correctly classified points out of total visited points. Change over 10 years, from 2006 to 2016, was explored by comparing class statistics from FRAGSTATS between our map and original land cover map. We found that natural land, i.e., forest and early successional, covered 33%, with 10% permanently protected, while human-modified land, i.e., agricultural and developed, covered 67% of the region. Over 10 years, natural classes increased, and cultural classes decreased by 5.8%. There were decreases for the three forest communities and increases for the two early successional communities. These changes are likely the result of natural recovery and disturbance, and conservation efforts by the Green Ribbon Initiative. Changes in habitat also came with distribution changes, e.g., increased fragmentation for some classes, which was readily visible. Our useful method measured functionality by emphasizing changes in composition and configuration. Our approach provides a tool for assessing cumulative regional-scale effects from site-level management and conservation. This large-scale view for conservation is needed to effectively mitigate future changes.