Ummm ...
Well, I've been doing hub-and-spoke tours since I was a child. My family travelled with bicycles. We'd stop somewhere for a few days and cycle out in different directions from there to see the area. I've been doing that ever since ... in fact, Rowan and I did another hub-and-spoke tour last weekend.
As for point-to-point tours ...
In 1990, my father and I rode 50 miles to a neighbouring town. My mother and my first-husband met us there ... my mother drove my father home, and my first-husband and I camped overnight. The plan was that I would cycle home and he would drive, but a huge wind storm blew in overnight, and so I took the lift home. So that was almost an overnight tour ... it had a cycling component and an overnight component.
In 1995, I cycled from Jasper to Banff over 4 days (3 days of cycling). I was supported by my first-husband ... he drove a van and leap-frogged me the whole way.
Then I think it was 1997 when I did an overnight MS150 tour.
That was just the beginning!