The merging process from an acceleration lane to the through lane of a motorway is an important aspect at interchanges, both in terms of safety and operating conditions. Several studies have demonstrated that the merging zones of interchanges are the main sources of interference between through and entering vehicles. In this context, incorrectly assessed gaps and headways can lead to severe crashes and traffic delays at interchanges. This study investigates the effectiveness of different countermeasures to improve the safety of merging zones and the ability of through drivers to adopt safe headways to vehicles entering from the motorway on-ramp. Four different countermeasures were tested in a driving simulator study: i) a gap metering signalization, consisting of a Variable Message Sign (VMS) and new pavement markings; ii) a static symbol projected on the vehicle's windshield by means of a Head-Up Display (HUD) that informed the driver to maintain safe headways to the entering vehicle; iii) a dynamic symbol based on Augmented Reality (AR) technology, built into connected vehicle technology, that provided additional visual information to the driver about his current headway to the entering vehicle; iv) the AR system was also tested with an additional audio warning. The driving behavior of forty-four drivers under the four different configurations based on the tested countermeasures was then compared to the driving behavior recorded under a configuration without any countermeasures (baseline condition). The results revealed significant positive effects of all the countermeasures, especially of the AR systems that helped through drivers to adjust their headway to the entering vehicle and thus the most effective solution for improving the safety of the merging zone. This study confirmed the great potential of AR and connected vehicle technologies to improve general safety conditions on the road network, especially in risky situations and difficult maneuvers.