I can tell you how NOT to do it. My PR was 42 miles and my first century was spur of the moment. No training, no planning, it took 11 hours, we started at 1:00 and got back to town at midnight, neither of us had adequate lighting for the trail. Headwind going out, darkness slowed us down coming back. It was quite an adventure. Here are some of the highlights.

My riding buddy is not the guy to ride with if you need a cheerleader. His encouragement was along the lines of "If we call my wife now, she can meet us at the next stop." I'd say "Do you think I need to stop?" and he'd reply "I am not going to make that decision for you" so being a bit stubborn I kept going.

We saw a copperhead. Since that ride I've seen a couple more, I tried to get a picture of one but my legs had other ideas and all I could do was glance back as I sprinted off.

Got to a trail town 5 min after the only restaurant closed. I wasn't hungry anyway.

Although not a cheerleader, my riding buddy kept up a steady stream of chatter the entire time. I alternated holding up my end of the conversation, listening, and tuning him out entirely. We agreed we had no idea what dark secrets we'd shared but that if I ever said "jail" he could respond with "hotel". (Sorry, I can't share those stories.)

I am planning my 2nd century. I decided I would wait until I had a brooks saddle, butterfly handlebars, gloves, & I'll start early morning. Most importantly it won't be spontaneous so I'll have adequate provisions, ie gatorade. I'm still debating whether to do it on the trail (former railroad, flat) or roads (hilly Missouri). I'd like to tackle the road, but maybe one victory at a time. I'll probably do it alone.