Roads remove habitat, alter adjacent areas, and interrupt and redirect ecological flows. They subdivide wildlife populations, foster invasive species spread, change the hydrologic network, and increase human use of adjacent areas. At broad scales, these impacts cumulate and define landscape patterns. The goal of this study was to improve our understanding of the dynamics of road networks over time, and their effects on landscape patterns, and identify significant relationships between road changes and other land-use changes. We mapped roads from aerial photographs from five dates between 1937 and 1999 in 17 townships in predominantly forested landscapes in northern Wisconsin, U.S.A. Patch-level landscape metrics were calculated on terrestrial area outside of a 15-m road-effect zone. We used generalized least-squares regression models to relate changes in road density and landscape pattern to concurrent changes in housing density. Rates of change and relationships were compared among three ecological regions. Our results showed substantial increases in both road density and landscape fragmentation during the study period. Road density more than doubled, and median, mean, and largest patch size were reduced by a factor of four, while patch shape became more regular. Increases in road density varied significantly among ecological subsections and were positively related to increases in housing density. Fragmentation was largely driven by increases in road density, but housing density had a significantly positive relationship with largest patch area and patch shape. Without protection of roadless areas, our results suggest road development is likely to continue in the future, even in areas where road construction is constrained by the physical environment. Recognizing the dynamic nature of road networks is important for understanding and predicting their ecological impacts over time and understanding where other types of development are likely to occur in the future. Historical perspectives of development can provide guidance in prioritizing management efforts to defragment landscapes and mitigate the ecological impacts of past road development.