The ride was about 2 and a half hours total with a stop to try to get U2 tickets(which sold out with only five people left in front of me, dammit). My feet started getting really cold right before I hopped back on the bike but then the numbness set in.
Thanks HereNT for the link to the Winter Cycling thread. I kind of figured that most of those guys rode clipless so I didn't bother to search, but I was wrong. It was really useful. I guess the most important thing is to to leave some room for my feet in my shoes. I might go out and buy a pair of shoes a full size larger and buy some of that crazy technical sox those guys were using.