My most memorable astronomy experience didn’t involve looking through an eyepiece, but watching some local children who were doing just that.
I’m a member of our local Public Library’s Board of Trustees in Northfield, New Jersey. In 2004, I persuaded the rest of the board members to purchase an 8" Orion Dobsonian telescope for 3-4 "Astronomy Nights" each year. The evenings would begin with a short presentation inside the Library, explaining what everyone would be viewing. Then we’d douse all the lights and go into the Library parking lot to peer through the scope.
The public response was tremendous, drawing 75-100 people each night. To accommodate all the crowds, we eventually added another 6" Orion Dobsonian and my own trusty 25-year old 4" Edmund Astroscan reflector. But the best part was watching the childrens' reactions to seeing the craters and lunar seas on the Moon, the rings of Saturn, the Orion Nebula and the moons of Jupiter.
Invariable, some child would say, "Wow, it looks just like the picture in my Science book," and I’d say, "Hey, you’re looking at the real thing now, the original!" Having grown up with video games and the Internet, some Board members thought the kids might be jaded and bored. But surprisingly, their sense of wonder was palpable, and the children were excited and visibly awed by the experience. Best of all, the Library’s circulation of astronomy books skyrocketed on those evenings, and we also had lots of questions about how and where to buy telescopes.
So that was my most memorable observing experience, even though I wasn’t looking through an eyepiece at all!