The tradition of having a wishing well near the park's iconic castle began, like so many things, at Disneyland. There it is Snow White's Wishing Well, which made sense because that castle was originally going to be called Snow White's Castle. None of the castles really match their movies; the Anaheim castle is famous based on the real Neuschwanstein and looks like neither the movie versions of Snow White or Sleeping Beauty's castles. Orlando's castle was based on several famous French castles and also doesn't look like its Cinderella castle namesake.
When the Magic Kingdom was built, many elements were copied from Disneyland. If it worked there, surely it would work here, right? There's logic to that argument, but it doesn't always translate well. The Wishing Well in particular is a poor translation. That's partly because Cinderella (the movie character) didn't wish at a well the way Snow White did, but it's also because the foot traffic in the Orlando resort is different. Not as many people come down this particular walkway, and when they do, they are moving down a steeper slope than in Anaheim, and thus they are somehow more business-like, more in a hurry, less easily distracted. The Wishing Well here lacks the charm of the Anaheim version--everything is more charming when it's smaller and surrounded by lots of trees and shrubbery, which is also missing in Orlando.
Still, it's a nice touch and not out of place. It's just not got the je ne sais quoi that Disneyland's version does.
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Kevin Yee is the author of numerous independent Disney books, including the popular Walt Disney World Earbook series and Walt Disney World Hidden History.