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I am looking for books/sefarim (Hebrew or English) that discuss the different months of the Jewish year, and their overall significance in relation to:

  • Zodiac Signs
  • Tribes
  • Chagim
  • Animals
  • Tanach/Chazal
  • Jewish Philosophy/Machshava
  • Anything else

Any recommendations would be appreciated.

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up vote 6 down vote accepted

"The Wisdom of the Hebrew Months", by R' Zvi Ryzman sounds like what you're looking for. I haven't read it myself, but I've heard good things.

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דבר יום ביומו has an introductory essay for each month, in which he explains the relevance of its associated tribe, zodiac sign, and Midrashic explanation (from Shir Hashirim Rabbah 7:7) of the words מה יפית ומה נעמת.

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The [series of] book[s] Chemdas Yamim contains a broad range of topics (philosophy, morality, custom, law), based on the special days of the year. Along the way, in several places it discusses significances of specific months, including Nisan.

Edit: Please note that, despite the disclaimer on the title page, some information is known about its author and the author was a Shabtai Tz'vi adherent. Views based on that influence are expressed in Chemdas Yamim.

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I've never read בני יששכר but I've heard a dvar torah or two on specific months quoting this book.

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The bnei Yisaschar is definitly a top source on the months/mazalot – avner Aug 24 '14 at 16:51

I can't recommend it (as I haven't read it), but Rabbi Nosson Slifkin wrote one.

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The Secrets of the Stars by Rabbi Ari Storch (Lakewood: Israel Bookshop Publications, 2011), by the author of this blog. A review of the book and a response by the author can be found here and here.

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Theres a good concise book by Rabbi Nathan Bushwick called "Understanding the Jewish Calendar". Its a good learning aid for understanding the calendar. It's split into two sections: 1) Astronomy (time, basic astronomy, the sun, stars, moon), 2) The Calendar (years and months, leap years 19 year cycle, the months, molad, molad zoken, holidays, adjusting the length of the year, two more dechiyos, the four gates, the sidros, the tekufos and the civil calendar).

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