I was going to grow my hair long again for the winter but until it reaches about a foot long it just goes into an eraserhead-style up-do. I'm not sure I can cope with a year of looking like the bride of Frankenstein.
As for cutting hair, in classical sources it is sometimes associated with mourning so Samhain would be a good time for a haircut in that respect. I know that in other cultures (modern Greece, Hinduism?) the hair is specifically not cut when in mourning, for up to a year. So you can pretty much take yer pick!
Rimmer: As my father always said, "Shiny clean boots and a spanking short haircut, and you can cope with anything." He said that just before that rather unfortunate suicide business.