It probably differs by culture and region, but I think the hardest holidays for teachers where I am are Halloween and Valentine’s Day. They are sugar-intensive, involve class parties or other in-school celebrations, and varying levels of participation from parents — something that can help or hinder, depending!
That doesn’t mean these holidays are all bad. If you keep your wits about you, you might even find yourself enjoying them. I enjoyed our school’s Halloween parade, seeing all the kids in costume. I enjoyed our school’s Valentine dance, which was actually an after school event; I liked when kids did the Cupid Shuffle with me.
I also got some Valentines from kids. These were two of my favorites: