06/13/2026
It was Friday night, I looked at Dempsey and said, “How can we surprise Aaron on Sunday?”
For context, Aaron and his friend had just spent 29 days hiking the Bruce Peninsula Trail. All 900 kilometres of it.
Not 90.
NINE HUNDRED - you read that right.
Their journey was ending in Tobermory, and somehow the idea of driving more than four hours each way to surprise him popped into my head.
Turns out my mom had the exact same
idea.
At first, I do not think Dempsey believed we would actually do it. But by 8:00 Sunday morning, we were in the car and heading north.
And honestly? The drive flew by.
There is something about spending time with people you love that makes long drives feel shorter and good conversations feel longer.
We arrived with plenty of time to spare, found the perfect hiding spot, and settled in to wait.
Or so we thought.
A text message from Aaron sent us briefly into panic mode. Lunch was abandoned. We ran back to the car.
There was strategizing. There was hiding. There was a lot of nervous excitement.
And then there was more waiting.
But when the moment finally came, it was worth every kilometre.
Watching Dempsey surprise someone he cares about after such an incredible accomplishment is a memory I will hold onto for a very long time.
The older I get, the more I realize that some of life’s best moments start with a simple decision.
Get in the car.
Make the trip.
Buy the ticket.
Say yes.
Life gives us plenty of reasons to stay home, wait for a better time, or convince ourselves something is too much trouble.
But some things are worth the effort.
Some memories are worth the drive.
And sometimes the best adventures begin with a slightly crazy idea on a Friday night.
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