I did this ride last year and really enjoyed it. Spokenwords comments are spot on. Especially about the navigating. I missed a couple of turns and had to stop and figure out where I was several times. It's particularly tough when you're towards the end and you're tired and not thinking as clearly. My nephew missed a turn at the end and finished the ride having done an extra 10-20 miles.
I went with my old custom steel frame with a triple chain ring 36/42/52 front and 11-26 cassette. I could have used a lower gear. My tires were 700x32's with about 70 lbs pressure.
The ride is really all about the scenery. It's simply breathtakingly gorgeous New England countryside and small towns.