Driver distraction is implicated in a significant portion of motor vehicle collisions; evidence has suggested that billboards can contribute to such distraction, but many knowledge gaps remain. The purpose of this study was to evaluate the effects of various types of billboards (static, 250-foot digital transition, 500-foot digital transition, and a control [no billboard] condition) and age group (teen, middle, and older) on visual behavior through the use of a driving simulator. To address gaps in the existing literature, the effects of age group and billboard type on the following visual attention variables were considered: percent of time participants looked at billboards, average glance length, number of glances, and glance pattern activity. Significant main effects of age group were found, suggesting that teen drivers exhibited significantly different visual behavior as compared to drivers in the other age groups. An Age Group × Billboard Type interaction for one outcome provided some evidence that percent of time spent looking at billboards significantly increased as billboard transition time increased for drivers, except for older adults, who spent more time looking at static billboards. This study helps lay the groundwork for future studies that may consider how young drivers’ differential scanning patterns impact driving safety.