My wife and I rode the Five Boro Ride in 2000. We had friends to stay with, so can't help you in that department. We went to the starting area and just sat there for about an hour. It just wasn't moving with 30K+ bikes. So, we went to another street and rode up to Central park and joined the ride there.
Somewhere on the route we heard a band playing, so stopped and had a beer and listened for a while, that was fun.
In many ways, it was fun and exciting and we're glad we did it. But we don't plan on doing it again. Problems:
- Hammerheads weaving through the bikes at speed. And many inexperienced riders, that were subject to do anything.
- Some of the ride was in interesting places, but most of it was in 'blighted' areas.
- While Doing the mile long climb up the Verrazano Narrows bridge was a bit of a challenge, it was white-knuckle time going down that fast with all those rides around you (many inexperienced).
We waited for the ferry from Staton Island for three hours in 93 degree heat with little shade - no fun.
But overall we enjoyed our trip to NYC. The day before the ride, we rode around the city, along the river paths and up to the top of the Brooklyn bridge. We stopped up there to take pictures. Just the other day we were looking at the picture we had someone shoot of us with the WTC towers in the background. Who could have known they would be gone a year and a half later.
Ken