I've found out that the crosstile script does not work with Crossover 13.1 - but some experiments allowed me to install Freeway 2 in a Win2000 bottle (cross tile tries a winxp bottle). This is with the original disks.
The game runs nicely, albeit only at lower resolution (read: I'm too stupid/winilliterate to get a higher resolution to work). A connected joystick (Cyborg 3D) is unfortunately not recognized. The friendly people at code weavers say that this is because early titles such as this did not use windows drivers, but read the port directly.
There are some animation artifacts when you are in the main hub, but the game is elf runs smoothly.