Few studies have examined the extent of driver sleepiness during a long distance morning trip. Sleepiness at this time may be high because of night work, waking early to commence work or travel, sleep disorders and the monotony of driving long distances. The objective of this study was to estimate the prevalence of chronic sleepiness (Epworth sleepiness score≥10) and sleep restriction (≤5 h) in a sample of 649 drivers. Participants driving between 08:00 and 10:00 on three highways in regional Australia participated in a telephone interview. Approximately 18% of drivers reported chronic sleepiness. The proportions of nightworkers (NW) and non-night workers (NNW) with chronic sleepiness were not significantly different but males reported a significantly greater proportion of chronic sleepiness than females. The NW group had a significantly greater proportion of drivers with ≤5 h of sleep in the previous 24 and 48 h, fewer nights of full sleep (≤4), acute sleepiness and longer weekly work hours. The NW group reported driving a significantly longer distance at Time 1 (Mean = 140.29±72.17 km, versus 117.55±89.74 km) and an additional longer distance to complete the journey (Mean = 89.33±95.23 km, versus 64.77±94.07 km). The high proportions of sleep restriction and acute sleepiness among the NW group, and the amount of chronic sleepiness in the NW and NNW groups reported during a long distance morning trip may be of concern for driver safety.