What to do on Sukkos, in the order you need it: which foods must be eaten in the sukkah and when you say leishev basukkah, what to do if it rains on the first two nights, sukkah decorations, how the lulav and esrog are bound and held, hoshanos, eruv tavshilin, and the bracha for each night.
What must be eaten in the sukkah. Bread or mezonos foods in the quantity of more than a kibeitzah — around the size of a medium slice of challah, 6 crackers, 2.5 sandwich cookies — must be eaten in the sukkah.
OU reviewChicken, meat, fish and cheese do not need to be eaten in the sukkah.
OU reviewBeverages (water, juice, coffee, etc.), fruit and vegetables do not need to be consumed in the sukkah.
Women. Women are exempt from eating in the sukkah. Women of Ashkenazic descent who sit in the sukkah should recite the bracha of leishev; women of Sefardic descent do not recite a bracha of leishev.
On mezonos. One who eats a normal amount of cake, cookies, pretzels, etc. does not recite the bracha. But if one is kovea seudah (a full meal), or one eats together with a group of people, then the bracha should be recited.
If one forgot. One who forgot to recite the bracha can still recite it whenever they remember, provided that they have not yet recited the bracha acharona.
How much rain counts. Rain is relevant only if it is dripping in the sukkah to the extent that if it occurred in the same manner in the home, one would change locations.
The first night. If it is raining on the first night, one should ideally wait an hour or two after nightfall before reciting Kiddush to see if it stops raining. If it continues, one should enter the sukkah with the family, recite Kiddush and Shehechiyanu, wash and eat one kezayis of challah (about one small slice) in the sukkah. The bracha of leishev basukkah is not recited. The meal is completed in the house.
The second night. If it is raining, one waits a short time to see if it will subside. If it continues, Kiddush and hamotzi are recited in the home after nightfall. One should eat a kezayis of challah at the end of the meal in the sukkah, but does not recite leishev basukkah.
They may not be used. One is forbidden to benefit from or use the decorations during all eight days of Sukkos. Decorations should not be taken down during all eight days of Sukkos, unless it is raining and one is worried that the decorations will be ruined.
OU reviewOne is allowed to change the location of the decorations from the schach to the walls of the sukkah.
How the set sits. With the spine of the lulav (the greenish side) facing you, the hadassim should be on the right side and the aravos on the left side. Hadassim should be higher up on the lulav than the aravos. The top of the hadassim and aravos should not be within four inches from the top of the palm spine.
Holding them for the bracha. One should take the lulav in their right hand. The esrog should be taken upside down in the left hand while both brachos — al netilas lulav and Shehechiyanu — are recited. After the bracha is recited, one turns the esrog back straight and shakes the lulav and esrog.
OU reviewLefties should hold the lulav in their left hand and the esrog in their right hand.
Shehechiyanu when the first day is Shabbos. Normally, on the first day of Sukkos, the bracha of Shehechiyanu is also recited. When the first day of Sukkos is Shabbos and we do not take the lulav on Shabbos, one should recite a Shehechiyanu on the second day of Sukkos.
Women. Women are exempt from the mitzvah of lulav. Women of Ashkenazic descent who shake the lulav should recite the bracha of al netilas lulav; women of Sefardic descent do not recite the bracha.
Afterwards. Lulav and esrog are not sheimos and, as such, do not need to be buried. However, it is not appropriate to simply discard mitzvah items in the garbage. There is a custom to save the lulav until Erev Pesach and burn it with the chametz.
What it consists of. An eruv tavshilin is accomplished by taking two already prepared food items. One of these items should be a cooked food (traditionally a boiled egg), and the other item should be a baked item (a challah roll or matzah). A bracha should be recited while holding the two prepared food items.
The order after Kiddush. After Kiddush, one should recite the bracha of leishev basukkah and then recite Shehechiyanu — the Shehechiyanu is also going on the new mitzvah of sukkah.
Havdala in the sukkah. Havdala should be recited in the sukkah. There are three customs regarding the bracha of leishev basukkah during Havdala.
Sources
OU review — the review notes three customs without deciding between them
Shemini Atzeres and Simchas Torah
The brachos. On the night of Shemini Atzeres, and likewise on the night of Simchas Torah, the correct bracha is lehadlik ner shel Yom Tov, followed by Shehechiyanu.
Tefillin. Those who wear tefillin on Chol Hamoed should remove them after Kedushah of chazaras hashatz. The shaliach tzibur on Chol Hamoed Sukkos should remove his tefillin before reciting Hallel.
Hoshana Rabbah — Pesukei D’Zimra. The Shabbos/Yom Tov Pesukei D’Zimra is recited, except that Mizmor L’Soda is recited and Nishmas Kol Chai is not recited.
Taking the sukkah down. One is not allowed to take down the sukkah on Chol HaMoed, even if they will not be home for the second days of Yom Tov, unless they are taking it down to rebuild somewhere else.
Compiled from Rabbi Sariel Malitzky’s “Review of Relevant Halachos for the Yom Tov of Sukkos” on the OU’s site (OU review). Nothing here is our own psak — every entry notes the guide it appears in. That review does not cover building a sukkah, the specifications of schach, or choosing daled minim, so those subjects are not in this checklist. For a personal shailah, ask your Rov.