Damn Frag, your sense of direction and map memory is something else! I recall you mentioned that recently, but seeing it in action is really impressive.
Thanks a ton Brian, but at the same, I'm not going to lie and instead say it's often because of having to try something more than once and getting the route in my head.
Truth be told I'm not really the type that seems to have a "GPS in my head". One of our ride leaders in the mt bike club I used to ride with can testify to that. He was also a snowboard instructor at one of the local mt pass resorts.
This guy would take us on rides that often had lots of brush here and there, a bit of downfall, and even what appeared to be dubious works of hikers or equestrians trying to keep us off the trails with clutter from clearing that was mysteriously stacked right in our way.
I'd often ask him, "How the heck do you always have your bearings in such a maze of trails?" He was usually pretty modest about it, but every once in a while he'd admit he was always pretty good at orienteering.
But me, if I led a ride that was in much worse conditions than expected, I would have a REAL hard time getting through it. The one time I can think of though was particularly bad, just after some forestry workers did some MAJOR clearing. There was one poor guy on my ride, and he was from opposite corners of the country, and no doubt regretted going on the ride. We had to walk through a lot of the clutter and it was very hard just to tell where the old trail was at times. I remember having to stop and yell back at him really loud to make sure he saw where I was at times.
I would never say risking getting lost on a ride is a bad thing though. One of the best rides I ever did was near a small town called Randle in South Washington on a very narrow singletrack trail that was clearly an old game trail. It's another ride I did with just one other person, a buddy I regularly rode with. It had spectacular views including meadows we'd go through with tons of wild flowers, and in particular one stopping point were we could see Mt Adams to the south, and Mt Rainier to the north. It was such a clear day and the base of the mountains was so close to the same color of the sky they looked like they were floating. The only thing either of us regretted on that ride was neither of us had a camera. We had to do a bit of walking at times to see where the trail picked up, but that was part of the fun.
The one major navigation tool I DO have when outdoors though is being able to read topographical maps well, which I always carried with me on my backpacking trips. I was on a particularly long ride once near Bend Oregon on a new trail a few guys had just built. They had marked turn points and gave us topo map copies. There was one point where we all stopped because suddenly there were possible turn points but no markers. Everyone insisted we'd gone too far and missed a turn, but I studied the map and said I think the turn is just up ahead. I offered to scout ahead and signal to them if I was right. Sure enough, that was where the turn was, and coincidentally just after that, one of the trail builders and main ride leaders came along after sweeping for any stragglers. He thanked me for steering the group the right way and applauded my map reading skills. The folks whom do outdoor sports in Oregon, which there are a TON of, are pretty skilled and really nice people.