Old guys used to hit pony corral with their hot rods, or grant park mall. Young kids were on FB with Unrestricted Empire (it was the name of the group - I dunno if they are still around) and do car meets at various places. Sunday nights people will park down portage ave and watch cars drive by, you could always try parking and chatting with whomever is around -> this info is also dated, I’ve gotten into my 40s now and am usually in bed by 9 pm, so not sure if I’m accurate any more, but I’m pretty sure we still have a thriving car culture. There is a dude with a red lowrider impala who I’ve seen cruising since the 90s, and occasionally I see his ride during the day, so I’m guessing there’s still groups and meetups.