09/18/2026
When I took my son to Disney for the first time, I cried in the middle of Main Street. Here’s why.
Unless you’re new here, you’ve probably heard the story…he was 5 when we took him to Walt Disney World for the first time. And because I apparently had complete confidence in my Disney-mom abilities, we started things off with Tower of Terror. 😂 Spoiler alert: He was TERRIFIED.
For the rest of the trip, he would cry before every ride because he was convinced it was going to be scary.
And honestly? It broke my heart.
I grew up going to Disney. These attractions were my childhood. They were magical. They were part of what made Disney feel like Disney.
So watching him be afraid of the very things I had been so excited to experience with him? It was hard.
But that’s not why I cried.
Because somewhere along the way, he got over it.
He started riding.
He started laughing.
He started getting excited.
And then I saw that face.
That pure, unfiltered, “THIS IS AMAZING!” kind of joy.
And standing there on Main Street, watching my son experience the magic I had hoped he would love someday… I cried.
Not because the trip was perfect. Because it wasn’t.
I cried because I realized that the Disney magic I had loved my whole life was becoming his memory, too. ❤️
And honestly, those are the moments I think about every time I help a family plan their Disney vacation.
Because sometimes the best Disney memories aren’t the ones you planned perfectly. They’re the ones you never saw coming. ✨