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We had a guy show up for a group ride without a helmet and when told he needed one went into a tirade about all the usual crap how its just as safe or safer to ride without one. Opinions aside our club liability insurance requires everyone wear a helmet or gtfo.
A local advocacy group does rides where no one wears a helmet. I doubt they are insured at all, so if someone gets hurt the members of the board are fucked.
A local bike shop has been running rides for several years now and last year they were smart enough to form a club under the local cycling authority so even though the club is free the ride leaders (typically shop employees) have liability insurance.
