Middle School Miles

Caves, Storms, and a Surprise Best Friend


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This episode of Middle School Miles is exactly what happens when school, travel, and life collide—in the most chaotic way possible.

After wrapping up a conference in Richmond, the journey turns into a whirlwind of long drives, wild weather (including snow and a midnight tornado), and unexpected moments along the way. But the highlight? Meeting a new friend and instantly becoming inseparable—complete with a sleepover full of late-night laughs and just enough trouble to make it memorable.

From exploring Colonial Williamsburg (and accidentally sitting on a cookie) to getting chased off a Walmart parking lot, the road trip continues through rest stops, food halls, and new destinations like Elizabethtown and Mammoth Cave—aka the “sketchy cave.”

Along the way, Sharlotte shares what it’s like balancing online school with life on the road, where schedules shift, mornings start late, and every day brings something completely new.

It’s a funny, honest snapshot of growing up while constantly moving—where learning doesn’t just happen on a screen, but everywhere in between.

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Middle School MilesBy Sharlotte & Stephen