There are a couple of TV series I know of that do this sort of thing. Check out Connections with James Burke, Modern Marvels, and Genius of the Ancient World, for starters. There's another TV series on Netflix that talks about stuff like the development of the bicycle, and the like, but the name escapes me. :(
If you're in the Bay Area, the Exploratorium and the Computer History Museum might be something you'd enjoy along these lines.
I'd add How It's Made to the list. Pretty interesting stuff. Doesn't go into the history very much, but sometimes touches on it to explain why something is done a certain way.
If you're in the Bay Area, the Exploratorium and the Computer History Museum might be something you'd enjoy along these lines.