You should send an email out to New York City Subway. I have heard their technology stack is pretty outdated.

Certainly if he's looking at local governments, MTA will be near the top of the list.

This article was pretty popular here a few months ago: http://www.theatlantic.com/technology/archive/2015/11/why-do...

Well, the actual switching and interlocking hardware might be a century old in places, but the computers are at most half of that. Hardly "oldest".