Have you thought of the Pacific Coast? It isn't starting from Chicago, but it is scenic for most of it, and it's not logistically impossible to complete it in chunks, as there are transportation options.
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Thanks to both of you for the input. I found out later this afternoon that there is an issue with the train tracks, so I may not get north of Seattle on the Amtrak. If they won't load my bike on the bus I may have to bail in Seattle, ride to Bellingham and connect to my route there.
For me it's partly about peace of mind.. If we don't lock the bike I lie awake in the tent imagining someone walking off with it. We will check out lighter alternatives to our big D lock and thick cable, but it sounds like we are a little more risk averse than some.
The L&C misses Glacier National Park, the jewel of the Northwest.
Thanks adventurepdx, that's the kind of info I'm looking for. Didn't know there was a shoulder. Do you by chance know if the should is cleaned much or does the wind do that? I figured the wind could be a problem, do you know the better times of year for less winds? Right now I'm thinking May or June.
Thanks for those links, adventurepdx! The links are very helpful; I've never heard of these groups before. I've checked Meetup frequently, but I agree with Biggus Duckus--there isn't much activity there. Yes, I'm relatively new to Portland. I moved here 1.5 years ago from Salt Lake City. I'm planning to bicycle the Great Divide Mountain Bike Route this July and also need to get in shape. It would be great to meet and ride with other fellow bicycling adventurers. I'm working on my terminal project for grad school this spring, so my schedule will be little packed until June, but I'm willing to organize some rides. Meetup.com seems like it would be an ideal venue to organize rides, but I'm open to other suggestions.
BUT... do you know you can get a gas burner for the Trangia?...In fact there are advantages over meths: controllable, no sooty pots...