Well, Chris:
Last year's Christmas music flip happened in Milwaukee while the little ghosts & goblins were still filling their bags with Trick-or-treat loot, on Friday, October (yes. I said October) 31.
WRIT (95.7) fired the first salvo in the Xmas music war, a couple of minutes past 3pm. WMYX (99.1) scrambled to get their first Christmas record on the air in the 4pm hour.
WLDB (93.3) didn't start "sprinkling" in holiday songs until mid-November.
I think even Chicago's WLIT (93.9), which is usually the first to turn on the Christmas light in the midwest, waited till November 10th or later.
I think one of the reasons the 2 stations flipped so early, is that 10/31/08 was the closest Friday to November 1st.
I anticipate that this year, they may wait till 11/6. It's so much easier to do it on a Friday & get it going for the weekend. If they do it in October again, I'll scream.