I had visions in my head back then of trying my hand at cyclocross racing. At the time I thought I might excel in the format. But to this day, I've yet to enter such a race and don't think I ever will. That ship has surely sailed.
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But why keep the Cross-Check rather than one of the others?
Well, it's kinda surprising, but, despite the fact that the Cross-Check, with it's rigid fork, dropbars, and 700x34 tires pumped to 55psi, is almost always a bike somewhat less than ideally suited to whatever ride you're on (ie: the wrong bike), it's also almost always an adequate bike for any given situation. It's not a cross country mountain bike, or a svelte road bike, or a long stable touring bike. But it can do all of these things. It won't always keep up with other bikes designed specifically for any of these aforementioned purposes, but it can handle just about anything you throw at it. It might be a little scary, or sketchy, or slow in doing it. But it can do it. As long as you've got the cojones to ask it to.
I know this from 15+ years of experience with this bike: If all you had in your quiver was a Surly Cross-Check, you'd be okay for doing most bike rides, at least the kinds of bike rides I like to do: swoopy singletrack shredding, lengthy gravel grinders, and longish road rides.
So, if I had to have just one bike, and if I didn't have my Coconino, I'd still say, "The Cross-Check, that's the one I'll push out of the lifeboat last." And I think that's pretty high praise.
Back in 2001, when this bike arrived as a frameset at the shop where I worked, I was still pretty fixated on old school parts and accessories. So, as with my Steamroller, I did my best to outfit the Cross-Check with a few cool pieces of old spec, like Mafac brakes and levers, a WTB Dirtdrop handebar, WTB shifter mounts, Shimano XT thumbies, a Suntour MicroDrive crankset, and a gun-metal blue and silver XTR M900 rear derailleur, which is, hands down, the most beautiful derailleur Shimano ever made.
Also of note is the fact that it's a bean-green Reynolds 631 Cross-Check, of which only a few hundred were made. They were only available for a short period of time in 2000-2001. Surly bikes are usually made of 4130 chromo, you see, so I think the boutique-y butted tubeset makes this particular bike somewhat uncommon.