Easy Halloween Hand Painted Glasses from All You
I saw these cute jack-o-lantern glasses over on Family Fun Crafts. They are hand painted, but you could use vinyl so that the glasses would be reusable on days other than Halloween. And if you don't have wine glasses you could use clear plastic cups and a sharpie to recreate the idea. Or you could use vinyl on just your punch bowl. I did vinyl faces on orange water jugs last year at our church Fall Festival and they were CUTE!
You can check out the tutorial for these hand painted glasses over on All You.