I am looking for cookbooks that explore the recipes for the foods associated with different holidays. I have just finished my Channukah selection, the חובות הלביבות and am going to start the text with instructions how to make food for Pesach, מצות עשה (not the version specific to grandmothers). I am not linking to the vegetarian cookbook as that food is not associated with a holiday. Or happiness. Or anything good.
Here are my go-to recipe books for all the major holidays of the Jewish year:
Every participant at the Pesach Seder needs to drink four cups of wine. Choosing good-quality wines without breaking the bank can be difficult. R. Moses Isserles' guide The Price of Wine is an invaluable resource. (It also comes in handy during the Purim season.)
Shavu'ot is the festival of the wheat harvest. There is also a longstanding custom to eat dairy foods during this holiday. I like to combine both of these elements using recipes found in R. Isaac Hai Taib's Milk and Wheat.
Planning the menu for the pre-Yom Kipur seudah hamafseket can sometimes be a little tricky. I like to get inspiration from R. Abraham Maimonides' HaMafsik LeOvdei Hashem ('The Concluding Meal for Those who Serve G-d').
On Purim, many eat triangular hamantaschen. I like to take this custom one step further and (referencing Psalm 22 and its connection to Purim) serve triangular venison. I follow the recipe of R. Elijah of Vilna in his The Three-Cornered Stag.
I highly recommend the שולחן ערוך's English version called "The Prepared Table". It is a wonderful book filled with quick recipes as well as ideas for how to set your table for various occasions - holidays, vorts, LeChaim's, shvigger's (mother-in-law) visits, and more. I will warn you that it comes in five hefty volumes, so you better be prepared to do a lot of learning and cooking.
There is an abbreviation version called "The Tour of the Prepared Table", which you may want to browse first.