I do a bit of side walk astronomy. Whenever I take the scope up to the blue mountains, we almost always stop at the three sisters lookout and invite whoever is there to come and have a look. It is educating for people who have no clue about whats above them as many are thrilled to know that the big bright star is actually Jupiter, or that the fuzzy patch under Orion's belt is actually a nebula, many light years away. The only downfall is that the light pollution can make it hard to find the faint DSO's, so I'm normally limited to bright DSO's and planets.
I have a 12" solid tube dob, and it confused one of the people looking through it, as he got down and tried to look through the bottom of the tube ("which end do I look through?"). Another person thought it was a hot water system and that i was here to install it, before he noticed the finder scope