Train Crews In Unfamiliar Territory

How often, if at all, do train crews end up operation in unfamiliar places? Do Railroads even allow that?

It's a federal rule, train crews MUST be familiar with the territory they are operating on. Train crews operating on unfamiliar territory in the case of a detour MUST have an employee on board who is familiar with the territory to act as a pilot.

On a related note. Do crews also have to be familiar with the loco type they are using?
In the UK the two knowledges are tightly regulated, with conversion courses required for new vehicle types (loco and MU); and route learning (normally done as a observer in the cab) required for new routes. These have to be kept up and expire after a period if not maintained by use.
For completely new lines, in extreme cases sometime the first driver (engineer) trainer will have to walk the line to learn the route before they can sign it off, drive it and then train others on it!

Yes, the route must be familiar. If a crew member has not run over a line, then he must take familiarization trips. At least one trip must be made in the specified time period afterwards. Our rule is that engineers must serve annually if the speed is 40 mph +, but 2 years on lines under that speed.

Some lines might have rules on equipment. I know that Amtrak has extra training if working on electric equipment. Most of the freight diesels have similar controls. There is nothing saying that I can't run any locomotive between a SW1, and an ES44AC.

In school they had mockups of EMD and GE electrical cabinets, and prime movers. This showed where all the resets are. This is easier now, since they are on a computer panel now (GE DID, and EMD EM2000). Further than that, they have a trouble shooter, whom I can contact via radio or telephone. Severe failures just result in towing the unit in dead. This is OK since we usually have multiple units. If not, they send out a rescue unit.

I'll put it this way: if you're a conductor and call for a pilot they will tell you "your engineer is your pilot". If you're a hoghead, and need a pilot....well they will give a few round trips and bam, you're on your own. My first time yarding a train in west colton I called for a pilot. They told me that they would send me a charge letter for working on territory I'm not qualified on. Problem is, I was qualified. All my qualification trips just happened to consist of mainline crew changes lol I never saw the yard. Same thing with Roseville. I'm qualified hold the RT17 which runs to Sparks and Portola. I couldn't tell you the first thing about that damn canyon. But I'm "qualified" lol