I have used several different map generators with varying levels of success; it seems many are designed for just world-level mapping. This is handy, sure, but when it comes down to maps of a valley or the area around a hill, there is a paucity of tools. I want to be able to generate (or create) contour maps, to give a realistic looking map to my players so they can see the surrounding area with elevation. Does anyone know of something that could work?

I am not talking about doing it by hand or with Paint, as my time is more valuable to me than doing it manually. Any suggestions?

Steal tactical maps from War Thunder, Call of Duty, Battlefield, etc... Put them in a tool like roll20, zoom in enough as to set a 1m scale grid and that's it...
Example:

While I have thought about that, I am not at all familiar with Roll20 (my group plays around a table) and trying to pick and choose already created maps may or may not fit the scenario or location I have in mind. I have been using MapMaker to draw the contour lines by hand, which isn't ideal but not a total waste of time, either. What I am looking for is something that randomly generates a contour map, to give to players as a "tactical" map that isn't just a few hills and rivers drawn with Microsoft Paint.

After searching around a bit this seems a likely place for you to get good answers. All of the topographical map generators I found produce maps from the real terrain of the earth. If you can find realworld locations that are close to what you want, try this generator .

Good luck!

Since i use roll20 for my games, it has built in map creation tools, if not try donjon.