This may seem a small thing, but it was big for me and since I've put my other milestones here I thought that I would add this one.
Yesterday I rolled my bike down the loooong gravel drive of the house that I am "house sitting" for the week without the slightest idea of where I was going! This was deliberate :) I rode 55.5 miles Saturday but it didn't feel like I had been on the bike at all (outside of a small saddle soreness) and a recovery ride seemed called for.
So I just turned the bike in a new direction out of their drive and just started riding. Eventually I found myself on a marked ride by my LBS so I just followed it for a ways, then eventually made my way back for a 20 mile ride.
It was a great ride - and the greatest part was being able to relax and enjoy the scenery without stressing over what I might run across on an unknown route. At some point I had a flashback of last December/January when I was relegated to practicing riding in a parking lot in the cold and wondering if I would EVER be able to really ride.
I've still a lot to learn on the bike - and that process probably never ends, but I am so glad that I made the leap and started in the middle of the winter because that gave me a little jump on the riding season.