Richmond first started being settled by English settlers in 1737 and was incorporated as the town of Richmond in 1742. "Montgomery" wasn't really established until well later, but, in 1716 there was apparently one Scottish guy in the area... and in 1717 the French built a trading outpost Fort Toulouse near the future site of Montgomery... so I assume that's where they got that date from.
Realistically I'd say that Montgomery wasn't actually settled by Europeans until the later 1810s. Fort Toulouse was only ever occupied by a handful of French colonial marines, not a proper settlement, not actually on the site of Montgomery, and by the 1740s it had been abandoned. Hard to justify tracing the history of Montgomery back to it. But... the non-inclusion of Richmond seems accurate, or at least it is if the cut-off is 1719. It might slip in to last place if there's nothing else between 1719 and 1737.
I may have not been clear when I switched from talking about Richmond to talking about Montgomery.
If we use the same standard for Richmond that would allow us to say Montgomery was first settled in 1716... then Richmond dates back to 1609, when the area near Richmond was briefly settled by some colonists from Jamestown, and making it the oldest city on the quiz.
If we use the same standard for Montgomery that dates the settlement of Richmond to 1737... then Montgomery wasn't settled until almost 1820, making it far too young to appear on the quiz.
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