Where do drivers look when approaching crosswalk locations with different sign and crosswalk treatments? This paper explores the gaze behavior of drivers approaching crosswalk locations at two study areas. The closed course study area evaluated the observation of traffic control devices (TCDs) placed in an otherwise sparse environment. The campus course area evaluated TCDs placed in visually complex environments. Driver gaze behavior was investigated to determine how TCDs were viewed in both day and night conditions as the drivers approached the crosswalks. Researchers found that drivers generally looked at crosswalk markings for a longer time at night than during the day at both the closed course and campus course locations. Nighttime observations of traffic signs were significantly longer than daytime observations on the closed course area, but not significantly longer at the campus course. In general, the crosswalks were found to capture more gaze time than the signs. Signs captured less attention and, in some cases, no direct eye-gazes during the evaluation time frame. When considering the gaze patterns when no TCDs were present, there were typically increases in gazes at the signs. It was observed that gaze values were generally higher for the closed course where there was no traffic and minimal distractions. Distractions and complex driving environments may shift drivers’ attention from the roadway and TCDs, thus requiring the design, implementation, and maintenance of TCDs such that they are easily interpreted and not visually dissolved in the abundance of visual disturbances of a complex environment.