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I put my pocket knife and my Glock 26 in the bottom basket area of my kids stroller. I re-holster in family bathroom. and have never been an issue.
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They're a little more thorough with strollers these days, speaking as an annual passholder with an 18 month old. Short of putting your gun under your baby, odds are pretty good you'll get caught.
Seems they're targeting the men a hell of a lot more than the women too. I go through pushing the stroller with my wife and daughters and they always make me go through the metal detector at magic kingdom. Never make my wife or daughters go through. Same thing when I'm actually carrying my 18 month old and we don't have the stroller. I'm also usually dressed in pretty standard khaki golf shorts and a dry fit polo. Nothing 5.11 or otherwise tacticool. Seems they are repeating this procedure with all of the white males coming to the park with young families. You know, us high risk types.
They make everyone go through at Animal Kingdom regardless, but Hollywood Studios and Epcot are a bit more selective. Rarely have to go through the metal detectors there.