Frek (a modified '82 Trek 614) has taken me on many 200k, 300k, 400k and 600k brevets. Between brevets and countless other "just for fun" rides, I can't even guess how many times we've gone over 100 miles together in a day. Quite a few.
The farthest I've ever ridden in a single day (i.e. 24 hours) was on my '85 Trek 760 that I foolishly sold a couple years back. Together we finished a 600k brevet in just under 24 hours. That was a
hard but very fun ride! My friend, Jan wrote a blog post about the ride
here. And here's the bike that made it possible (picture is from a different ride closer to home):