Hmmmm.... If the NYO&W still existed the O&WRHS logo would certainly be infringing, particularly since they claim class 39 (Transport) in which the NYO&W would have clearly had their trademark. If you used the NYO&W circle mark without the horizontal bars, you could probably claim that the trademark has gone into the public domain. For their part, the O&WRHS would claim that theirs is a new, distinct mark from the lapsed NYO&W, that they're not profiting from licensing the trademark, and that if you'd only ASKED, they'd have given you a license for free. Given that their first use in commerce date is 1986, they're not claiming to be the owners of the NYO&W circle mark.
The O&WRHS have a pretty strong claim to their trademark. I don't know of anybody who claims the old Erie logo as a trademark, or any new derivative mark.
Hope that helps.