Crashes between vehicles and trains at highway-rail grade crossings are low in number but are catastrophic events typically involving multiple fatalities and serious injuries. Advances in driving assessment methods, such as the development of on-road instrumented test vehicles, now enable researchers to understand driver behaviour at such crossings in ways not previously possible. This paper describes a study conducted to explore factors that shape driver behaviour at rail level crossings using instrumented vehicles in metropolitan and regional locations. Twenty-two participants drove an On-Road Test Vehicle (ORTeV) on a predefined route in regional Australia with a mix of both active (flashing lights with/without boom barriers) and passively controlled (stop, give way) crossings. Data collected included driving performance data, head checks, and post-drive interviews to capture driver strategies. While the focus in this paper is on the head check data, the data from the full suite of integrated methods clearly demonstrated how behaviour differs at active and passive level crossings, particularly for novice drivers. For example, head check data show the reliance and expectancies of novice drivers for active warnings even when approaching passively controlled crossings. These studies provide novel and unique insights into how level crossing design and warnings shape driver behaviour.