2x2hr vs 1x4hr - Endurance Adaptations

Yes, as I have commented before.

In my own case, I went from never riding more than 2 h (two laps of Galveston Island) at a time for 6+ y to doing significantly longer rides in Maryland. For the first year I had neck pain after 3-4 h, but it went away as I started doing more long rides (one of the first being a 6+ h sojourn on a newly-acquired tandem…the guys we fell in with just kept claiming, "it’s just a little bit further, keep riding with us!).

Prior to that, I tried to steal the Missouri state RR on a borrowed bicycle after only training on a rubber block-pedaled stationary bike 7 h/wk for 6 mo (my bike had been stolen around Christmas, and I couldn’t afford to replace it). I dropped the last of my all-day breakaway companions with 20 mi to go, only to be caught and then worked over by five guys from the same team with just 5 mi to go. My legs held up just fine, but my hands, feet (back in the toeclip/toestrap days), and neck (from holding up the weight of my head plus a helmet) were in agony. Still beat one of them, though!

Why is it that my strongest cycling memories are of the most painful moments?

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Not sure how it all works, but it’s definitely true. Moments that are impossible to forget.

The most memorable ones always have something like that, sometimes its the weather like unexpected snow coming down heavily as you crossed a mountain pass during an event etc.