I'm Jewish, and my elementary school music teacher was Jewish, and he organized Christmas caroling and taught the school choir Christmas songs, and one or two Hannukah songs and organized a Christmas concert. So much for the good old days.
Perhaps that's because observant Jews tend to be conservative politically too, and secular Jews tend not to be.
There's hope. My children moved into public school this year in Mississauga, and when we went for parent-teacher interviews a week ago, there were trees and Santa and Christmas references everywhere. My 9 year old daughter showed me the song list for their concert, and lo, some traditional tunes are on the list - it was made up of kids requests.
Plus there was a Chanukkah poster on the entrance door (some reference to "faith forward in Peel" on it). My daughter is probably the only Jew in that school, but it made me feel good. Another positive sign - of the books they've read in class this year were "Number the Stars" and "Hana's Suitcase". Maybe it's an exception, but it's possible the pendulum is swinging to where it should be.