I don't completely know what to say about On the Road. It was an okay read, although I had trouble staying awake throughout as it was so random and without any real meaning. This book did not differ from other books that are considered "classics" but have been written within the past 100 years or so, it was not good. The writing is different, that doesn't mean it is good, it is just non-standard.
The beat generation was mostly a bunch of drug addicts who didn't know what to do with themselves. I feel like every generation has a feeling that they are different than those generations that came before, and because of this they try to find themselves through some kind of existential experience. The idea of this book is that traveling and expressing oneself completly in all situations is one path to finding IT. What is IT? Well you just have to know right?
Seriously though, this book was mediocre, it was interesting only in that it was original and is a defining piece of work of that particular group of people within that particular generation. I am not sure I would say that I recommend reading it if you are really looking for a good read, but if you want to check something by Jack Kerouac off your list then by all means give this a shot.