“Beware thoughts that come in the night.” That admonition starts off William Least Heat-Moon’s book, Blue Highways. He wrote those words a little over a quarter of a century ago as he set up on a 13,000 mile journey across America after separating from his wife and losing his job. I read Blue Highways years ago. It, together with Zen and the Art of Motorcycle Maintenance, On The Road with Charles Kurault, and Then Came Bronson, weave together into a dream I’ve had of going on the road myself, in finding out a little bit more about me, about the people around me, and maybe, just maybe, being able to say a word here or there that might help someone.

Ten years ago, my first marriage ended, yet unlike the great travelers I so admired, I had kids to be concerned about. It is hard to hit the road with an eight year old and a five year old. So I stuck it out at my job for another few years. I remarried and we had a daughter of our own.

My second wife and I met online and as I look back over the past ten years, while I haven’t had the opportunity to write the next great American Travelogue, I have traveled extensively online. I sit in a small office in a rented house just outside of New Haven, CT reading what people around the country write, writing my own blog posts and doing consulting here and there.

At night, I toss and turn, looking for that path which will set things right. I continue to dream of travels, but Fiona is now turning seven and my responsibilities keep me tied to this town. Then, one night, came one of those ideas that Least Heat-Moon warns about, The Long Blue Trail. I could trace Least Heat-Moon’s travels, perhaps mix in a little Kerouac, Pirzig, Kurault and others into a journey into cyberspace.

I could find pictures, videos and blog posts, following, as closely as I can make out, Least Heat-Moon’s trip. I could include some Google Maps or other content to help tie it together in a mix of hyperlocal citizen media, placeblogging, and simple posts from regular people.

I would follow the Blue Highways of Cyberspace, not the Interstates. DailyKos and Huffington Post, these are cyberspace’s Interstates. Everyone goes there. You know what you get when you stop there. No, I’ll search out the websites with no page rank, the millions of bent and narrow rural American cyberroads.

There is where the Blue comes from. The Long Tail part comes from Chris Anderson where he talks about all those websites that aren’t on the A-List, that don’t have high page rankings, yet make up the majority of cyberspace.

William Least Heat-Moon hit the road in 1978 in a Ford Econoline van that he had outfitted for the trip. The book didn’t come out until 1982. Things are a little different these days and so I’m starting off my journey a little bit differently. I’m writing it as I go and posting it online. It may be harder to monetize this way. It may turn out to be another one of those grand adventures where I make it to the edge of the virtual town, and after a few posts, lose steam and abandon it. We shall see.

So, I’ll start off by posting it as entries on my blog, Orient Lodge. If I get past a few entries, it will become its own category, then its own website and we’ll see where it goes after that. Wish me luck.