Some of the most fun things I've done in aviation weren't done in an airplane. Instead, they involved no cost at all except for the dozens of hours I've spent on them. That free fun was nothing more than looking at a sectional chart and imagining flights.
Sometimes it was trying to picture was some interesting geographical feature on the chart would look like from the air (or seeing what some strange place I came across on Google Maps would look like on a sectional). Other times it would be trying to figure out how to deal with an odd or challenging bit of terrain. Or it could be some oddly-shaped or complexly-layered airspace and trying to figure out why it was laid out that way.
Usually those diversions don't come from intentionally sitting down and randomly picking a place. Instead, they tend to come from tangents during flights I was actually planning at the time. For example, this straightforward fictitious flight came from an NDB that happened to catch my eye while I was planning a flight to St. Louis Regional Airport (KALN):
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You don't even have to be able to read a sectional chart at all to see what's amusing about that short flight. All you need is a basic familiarity with the TV show The Simpsons. If you want to play around with a more interactive version, check it out on on the free flight-planning tool SkyVector here.
If you're not a fan of The Simpsons, you can always just fly to pizza instead. (Yes, I said fly TO pizza, not fly FOR pizza.) I just hope you don't like fancy ingredients, because it looks like all they have is plain.
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Last but not least, I can't leave out the most famous of oddballs, the Crazy Woman VOR in Wyoming:
Do you have a strange or unusual place you've come across? Share it in the comments.
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