NYC to Philadelphia (145mi, 160mi total). Longest distance I've gone so far. Heard about a local group that does very long rides, so I decided to join them the day before. They were super friendly and helpful, a real nice riding group. We started with about 40 people... some would meet along route, some had to drop out and in the end about half reached the destination. There were all types of riders, a wide range of bikes (a handful of single speed riders) but all were pretty capable.
The map:
View of NYC from across the Hudson
Had a wild crash and somehow I landed on my feet. At about 17 mph, my front caught an embedded train track, which threw the rear of the bike up. The rest of the bike would swing 180 degrees but the crank landed right on a curb. That broke my momentum and I landed in a crouching position. There's a small dent on the rim below that gash, and my seat was pointed all the way down.
Anyway, most of us took the train back and we were greeted with rain. I had brought along a Brooks seat cover and it did not fare very well, so rode the last 8 miles standing up. No regrets.