The Observatory Track is a track that is unlocked in Chapter 4, which leads from behind a broken wall next to the Library to the abandoned Observatory and the Football Field. It is used heavily in Stronghold Assault. Aside from missions, no students are ever seen here.

It also gives access to the tunnels system that allows Jimmy to get to the Happy Volts Asylum and Blue Skies Industrial Park directly from the school. The player must first complete Galloway Away to get access to the Happy Volts Asylum.

The exact use of the track is unknown, given its relatively rough nature and having multiple speakers placed around in parts, it may have been a former cross-country running track.