Is swimming still allowed at the Pond in October. I understand that it may now be unsupervised i.e. no lifeguards on duty.

Swimming is allowed year round at your own risk. Many open water swimmers come here. It's chilly but not cold. Most have on wet suits at this point.

I'm not completely sure of the proper rules, but if you felt like diving into that CHILLY October water, I don't think anyone would stop you. I'd say it would definitely be "At Your Own Risk".