'Chalaka' Haircut on Chol Hamoed
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Question
My son will turn 3 during Chol Hamoed. Should I cut his hair today before the holiday or during Chol Hamoed?
Answer
Hello and Mazal Tov
Although haircuts are generally prohibited during Chol Hamoed, the haircut given when a child turns 3 is permitted during Chol Hamoed. In fact, some have the custom that if the child turns 3 before the holiday, they wait and perform the haircut during Chol Hamoed.
However, you should not go to a barber who charges for the haircut, unless the barber is poor and needs the money for the holiday itself. If you do not have such a barber, find someone who will cut the hair for free.
Source
Shaarei Teshuva (Siman 531); Shu"t Peulat Tzadik (Maharitz, Part 3, Siman 248).