It’s not specific to Bend or Central Oregon, but on Christmas Eve we enjoy NORAD Tracks Santa—the "official" site for finding out where Santa is right now. The dynamic map is updated every few minutes with Santa’s current location, and every so often a video goes "live" showing Santa flying around near a famous landmark.
If you have kids, they’ll be glued to it. Heck, even I’m glued to it at times.
I don’t know if Bend will show up on the locations; you never know!