The book starts off well with Kerouac meeting a young student of Zen Buddhism called Japhy Ryder and the two decide to climb the Matterhorn. I've been out to the Sierras myself and enjoyed the descriptions of the scenery, it reminded me of my time up there, sleeping in the forest, waking up in my sleeping bag covered in snow. It's really beautiful writing, and the story (a rarity for Kerouac, having a story) rushes forwards. There's also a nice buildup with Kerouac hopping freights, sleeping on beaches under the stars, etc. It's what makes Kerouac the writer he is. Kerouac, Ryder and Ginsberg have some nice back and forths debating poetry. Ginsberg's cynicism of Buddhism makes for an interesting and funny debate.
After the Matterhorn episode though, around page 80, the story is basically told. Kerouac has no idea how to progress the remaining 100 pages. I guess the point of the book was to talk about Buddhism but I never felt Kerouac was a serious student of it. Buddhism promotes abstinence of sex, drugs, drinking, all of which Kerouac partakes of frequently. He's like a lot of people I know who are into Buddhism - they take the parts they like and pretend they're the real thing. They're not, and neither is Kerouac.
Unfortunately, Kerouac's writing becomes even more meandering as he rambles on with pseudo-profound writing. Here's an actual quote which he thinks is enlightening: "Form is emptiness and emptiness is form and we're here forever in one form or another which is empty". See what I mean? And this goes on for 100 pages!
"On the Road" wasn't as revelatory to me as it was to some of my friends. It was disjointed, a bit annoying, not nearly as clever or interesting as it thought it was and ultimately quite boring. 10 years later, I decide to give him another try with "Dharma Bums" and initially I thought it was going to be great. What happened was that Kerouac's enthusiasm and naivety got in the way of the writing.
It would be too easy to type down passages from the book that shows how shallow the book's attempts at mysticism are or how Kerouac's writing makes him sound like a wide eyed innocent and inexperienced 13 year old from the country setting foot in the city for the first time. Suffice it to say, if you didn't like "On the Road" you won't like this. Nor will you if you are a student of Buddhism. If you like Kerouac or are 15 years old, you'll probably get a kick out of this.