1. At what age is the haircutting ceremony to take place?[1]

Many customs exist regarding the date of the child’s first haircut. In the sources, the following ages have been mentioned as appropriate for the haircutting of the child: Nine months[2]; Two years of age[3]; Three years of age[4]; Four years[5]; Five years[6]; 6-7 years old[7]. Different communities have adapted different customs in this matter. Practically, the widespread custom today[8], as well as the Chabad custom[9], is to cut the child’s hair at age three. [See above in Chapter 1 Halacha 1 for a lengthy Midrashic and Halachic explanation behind the significance of specifically age three.]

The third birthday is a unique opportunity and an auspicious time for the education of the child.[10]

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[1] See Nitei Gavriel Chapter 2:1-2 footnotes 1-4 regarding up until age 3 and 3:1 regarding age 4 and onwards, for all the customs on the matter

[2] Heichal Avodas Hashem 2:179

Thirteen weeks of age: See Leket Yosher p. 97 that the Terumos Hadeshen would allow to cut the hair of a child of thirteen weeks. However, clearly, the intent there is regarding hair that has been left to grow for thirteen weeks, and not at age thirteen weeks. [Nitei Gavriel 2 footnote 1 unlike other Melaktim]

[3] Peulas Tzadik 3:236; Custom of Teiman; Poland; Lita; Gur; Square; Steipler

The reason: Avraham made a Mishteh for Yitzchak at age 24 months celebrating his weaning and beginning of his education. [See Bereishis 21:8; Midrash Tanchuma Vayeira 22:3] Shmuel was taken to Shilo at age 24 months. [Shmuel 1:1-11]

[4] Shivim Temarim 68; Siddur Maharid end of Vol. 1 p. 169b that so is implied from Kisvei Arizal; Arugas Habosem 210; Maharam Brisk 2:98; Afrakasta Deanya 161; Igros Kodesh 7:235; 11:60 and Likkutei Sichos 22:329 that so was directive of Rebbe Rayatz and it was seemingly a tradition from many generations; The Alter Rebbe had his Upsherinish on his third birthday [Likkutei Dibburim 3:481]; The Tzemach Tzedek had his Upsherinish on his third birthday. [Sefer Hasichos 5700 p. 40]; Nitei Gavriel 2:2 footnote 3; Minhag Ruzin; Belz

The reason: There are several connections between the age of three and the start of the child’s education: 1) Arla: In the Mitzvah of Arla, it is prohibited to benefit from the fruit of the tree for its first three years, while in its fourth year the fruit is to be consecrated and brought to Jerusalem to be eaten. [See Kitzur Shlah; Elya Raba 17:2; Shaareiy Teshuvah 17:2; Yalkut Shimoni and Midrash Tanchuma, Parshas Kedoshim, sec. 14; Panei’ach Raza (Parshas Kodashim); Arugos Habosem 210] 2) Tzaras. When the Torah mentions the term והתגלח/And he shall remove his hair, the letter gimmel is oversized.  [Hagahos of Shlomo Ahron Wertheimer on Midrash Rebbe Akiva] 3) The age of three years old is associated with Chinuch of a child: See Tanchuma Vayeira 22:3 and Titzaveh; Pesikta Zutrasi; Tanchuma Tetzaveh; Admur in Hilchos Talmud Torah 1:1; Michaber 245:5; Rambam Talmud Torah 1:6; Sukkah 42a

[5] Keser Shem Tov [Gagin] p. 591 [custom of Eretz Yisrael]; Even Sapir 2:47; Igros Kodesh 7:235 in name of Keser Shem Tov ibid [although concludes that perhaps it is a printing error and should say 3] 11:60 that so is custom of some Sephardim; Nitei Gavriel Mavo p. 24 that so is the custom of Russian Jewry

[6] Shulchan Gavoa 31:12; Kaf Hachaim 531:30

[7] See sources in Nitei Gavriel 3:1 footnote 3; Nitei Gavriel Mavo p. 24 that so is the custom of some Sephardim

[8] Arugas Habosem 210; Maharam Brisk 2:98; Afrakasta Deanya 161; Nitei Gavriel 2:2 footnote 3; Minhag Ruzin; Belz

[9] Igros Kodesh 7:235; 11:60; 22:336 and Likkutei Sichos 22:329 that so was directive of Rebbe Rayatz and it was seemingly a tradition from many generations; The Alter Rebbe had his Upsherinish on his third birthday [Likkutei Dibburim 3:481]; The Tzemach Tzedek had his Upsherinish on his third birthday. [Sefer Hasichos 5700 p. 40]

[10] Igros Kodesh 11:5