I rode along with a guy that was doing this a few years ago. He had taken up biking as a way to lose weight and wanted to do this as a goal and challenge. The gap in the GAP hadn’t been completed yet so we did laps from the Glenwood Bridge on down to the state penitentiary. He had parked his car in SouthSide park and had food and water stashed so he could fuel up without leaving the trail. I joined him at about the halfway point and stayed with him until he got his 100. He was exhausted but extremely happy that he made it. As you can imagine it gets boring riding in circles, so having someone to talk to makes it a little easier.