Virtual reality technology can be used for ecologically valid assessment and rehabilitation of cognitive deficits. This article expands the scope of applications to ecologically valid multitasking. A commercially available driving simulator was upgraded by adding an ever-changing sequence of concurrent, everyday-like tasks. Furthermore, the simulator software was modified and interfaced with a non-motorized treadmill to yield a pedestrian street crossing simulator. In the latter simulator, participants walk on through a virtual city, stop at busy streets to wait for a gap in traffic, and then cross. Again, a sequence of everyday-like tasks is added. A feasibility study yielded adequate “presence” in both virtual scenarios, and plausible data about performance decrements under multi-task compared to single-task conditions. The present approach could be suitable for the assessment and training of multitasking skills in older adults and neurological patients.