Those Folks in the Past Talked Funny

Ye Olde Trip to Jerusalem proudly calls itself "The Oldest Inn in England." The inn purports to have opened its doors for business in 1189, and it's been going strong ever since. Their name would seem to indicate that this spot is where people began a pilgrimage to the Holy Land.

Except, of course, that's not at all what it means. From Ye Olde Trip to Jerusalem's website:

Many people believe the pub is named ‘Ye Olde Trip To Jerusalem’ because people made a trip to Jerusalem from here. In fact the word “trip” does not mean a journey in this case. An old meaning for ‘trip’ is a stop on a journey, like being tripped up, so the inn’s name means a stop or rest on the way to Jerusalem. Why not follow in the pilgrims tradition and pop in on your way past the pub for a quick pint or a nibble?

Wait, what? A "trip" is not going someplace, it means stopping someplace? Aren't we using English here?

It's not something we often think about when we consider the past, but how well would we even understand what was being said? Conversely, would people from the distant past understand what we would say?

Not to throw cold water on time-travel movies and books, but if you and I were to hop in a time machine and set our destination anywhere from 500 to 1000 years ago, we would find ourselves with a Cool Hand Luke problem...a failure to communicate:

And, don't even think about using Google Translate. Coverage in the middle ages was spotty at best.