I did a series of 3 road trips close together this summer, but the really crazy part was that I planned a late night right before we left for the first one.
I took Chloe and 3 friends to see Jurassic Park at an outdoor showing at Deerfoot Mall. It was chaotic at first, but turned out well. We spent 90 minutes in a traffic line only to not get into the parking section, but luckily I had brought some chairs so we set up in the front with chairs and sleeping bags, which ended up being the best spot anyhow.
The girls ate in the food court inside the mall, and shopped around until 9pm. It was still another hour after the stores closed before it was dark enough for the movie, so they played cards until the movie started.
It was a super fun 1:00 am kind of night, and probably a once-in-a-lifetime experience. (At least with this mom.)