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One which sticks out to me is when I first played Blue, though it's not particularly exciting. After finishing Silph Company, the next stop for me was Fuschia. Going east from Vermillion past all the bikers and gamblers, past the repair crew working on the Snorlax-shaped dent on Silence Bridge, and continuing south along a lovely raised wooden walkway above the ocean, battling some fishermen along the way. Follwing the elevated Bridge southward, it eventually terminates West beyond a forest, back onto solid ground, and then you're met with a labyrinth where are so focused on getting out, that you lose sight of the ocean. Navigating this section took me a long time. Eventually you make it out and continue southwest along the coast with a regular, open route. I remember all the trainers along here being bikers and bird users. Looking at maps, there is also a distinct lack of wild grass. It's basically a trainer gauntlet.
One reason this route is such a vivid memory is because it was nighttime when I finished, had been playing for hours on my original Game Boy, and so had developed a migraine. I just wanted to get to Fuschia, and I remember struggling with the labyrinth, so I was struggling with only scraps of HP and PP as I inadvertently activated a trainer battle.