This is not the dumbest but probably my most memorable travel story.
I was at a company seminar in Vegas in December of 2008. On Wednesday afternoon, I take a cab to the airport and arrive in time for my flight. As I am walking to my gate, I notice that a number of flights are cancelled. No worries, I keep walking and outside the terminal windows, I see flurries starting. Hmmm...Vegas and flurries. I reach my gate just in time to see the "Cancelled" sign go up. After spending about 30 minutes in there, I speak to my fellow travellers and hear that this is the first snow in Vegas in 16 years and of-course there isn't any snow clearing equipment. Incoming flights were being given priority over outbound flights.
So, I trudge with my strolley to the taxi line, which had swelled to maybe 200 people by then and go back to the Venetian, where I checked out of. I then spend the next 3 days on the phone with my travel agent, sleeping, gambling and getting wasted on the company dime. Finally, my agent is able to buy a one-way on Jet-Blue to JFK. I reach there past 1 am on Sunday morning, give a fellow passenger a ride to EWR to pick up his car and make my way home in NJ.