Work zone safety has been a major concern for drivers and transportation agencies. Considering the severe consequences of crossover work zone crashes coupled with the limited literature on the median opening length, this paper aims to investigate the influence of the median opening length on driving behaviors from a behavioral perspective in crossover work zones. A driving simulation study with 32 participants was carried out to investigate the driving performance by metrics (speed, acceleration, maximum steering wheel speed, and lane-changing trajectory) with respect to five median opening lengths. The significant differences of each driving performance metric among various median opening lengths were found in the process of crossing through the median opening on the entrance by-pass and exit by-pass. The results indicated that drivers’ speeds were always higher than the speed limits for all median opening lengths. A narrower median opening may induce risky driving behaviors such as sharp deceleration and decelerating while lane-changing, which may increase speed variance. When crossing through the median opening with a larger length, high speed variance, sluggish lane-changing operations, and improper lane-using behaviors were observed because the excessive lane-changing space provided by the larger median opening length would decrease the situation awareness and increase the speed preference heterogeneity among drivers. Finally, some traffic management strategies were proposed, which can improve the safety and mobility of crossover work zones and further provide a basis for the formulation of related standards.