Street-yes
Park-no, unless I'm the only one in there then I'll listen to music. I can't listen to music when I'm trying to ride the park and a bunch of skateboards and bikes are all around me.
Yes, get some good earbuds (senheiser) and they wont fall out. And the one you leave out put under your shirt and it wont fly about. Easy way to do it is put them up your back and around your neck, not up the front....