The Old City ward of Docktown contains a variety of partially unearthed ruins of what was once part of the downtown area of Docktown. (The Downtown Ward is another part of the former downtown, excavated and re-inhabited earlier.) It is the site of extensive excavations and considerable recent, hurried development. Aside from a tiny section (comprising part of the campus of Eastern Ponyland University, the Old City was essentially uninhabited for much of the Dark Age.

Formerly, part of the Old City Ward was the Walled City Barony. This self-sufficient fortress was incorporated into Docktown peacefully, with its baron becoming a member of the Docktown Governing Council.