Work zone safety from a psychological perspective has received little attention in scientific literature. Therefore, the present study aims to explore the influence of roadwork characteristics and drivers’ individual differences in terms of personality traits and self-assessment of driving skills on speed preferences in a rural work zone. Eight hundred forty-five Norwegian drivers stated their preferred speed for ten pictures of a rural work zone with a 50 km/h reduced speed limit without knowing the speed limit. The results showed that the preferred speeds were greater than the actual reduced speed limit for all pictures. The standard deviations were quite high (from 11 to 14 km/h), indicating that drivers have a rather high variation in preferred speeds. A multilevel model was used to analyse the effects of the variables on speed preference. The results indicated that preferred speeds increased with age, higher scores on the normlessness scale, and higher self-assessment of own driving skills. As for the roadwork characteristics, speed increased with the presence of road markings by 11 km/h, while it decreased by 9 km/h with the presence of road delineators and by 5 km/h with barriers. Implications for respect for the reduced speed limits in work zones were discussed, and recommendations of other countermeasures were presented.