Megillot
The five biblical scrolls read on five different occasions — most famously the Megillat Esther on Purim.
Summary. The Five Megillot are biblical scrolls read on five holidays: Shir HaShirim (Song of Songs) on Pesach, Rut (Ruth) on Shavuot, Eichah (Lamentations) on Tisha B’Av, Kohelet (Ecclesiastes) on Sukkot, and Esther on Purim. The most prominent in practice is Megillat Esther, which is read from a klaf (parchment scroll) on Purim night and morning. A kosher Megillat Esther scroll is a substantial purchase; many shuls own one and lend or sell privately produced ones to congregants. Reading from a printed text is a fallback if a kosher scroll is unavailable, so that the reading is not skipped — but the blessings are omitted in that case, and the mitzvah is only fully fulfilled by hearing it read from the klaf.
The Five Books
Shir HaShirim — Song of Songs. Read on Shabbat Chol HaMo’ed Pesach (or on Pesach itself when it falls on Shabbat). Many Chassidim read it every Friday afternoon, in preparation for Shabbat; among many Sephardim the custom is to chant it on Friday night, before the evening service. The Rambam (Mishneh Torah, Hilchot Teshuvah 10:3) reads its erotic poetry as the supreme allegory of the soul’s love for God.
Rut — Ruth. Read on Shavuot. The story of the Moabite convert who becomes the great-grandmother of David is the paradigmatic Jewish narrative of chesed and conversion. Tradition holds that David was born and died on Shavuot.
Eichah — Lamentations. Chanted on the night and morning of Tisha B’Av in the special, mournful Eichah trope. The book is a poetic lament over the destruction of the First Temple in 586 BCE.
Kohelet — Ecclesiastes. Read on Shabbat Chol HaMo’ed Sukkot. The most philosophical book of Tanakh, traditionally attributed to Shlomo HaMelech in his old age.
Esther — Esther. Read twice on Purim: once on the night of Purim and once on the morning. The mitzvah is to hear every word, hence the importance of a competent reader. A Megillah without God’s name explicit but with God’s providence on every page.
The Megillah Scroll
A kosher Megillat Esther scroll, hand-written by a sofer on parchment in STaM script, costs $500–$5,000 depending on size, quality, and decoration. Unlike a Torah scroll, the Megillah is not rolled between two rollers for reading. Instead it is unrolled and folded accordion-style — like a letter, echoing its origin as a dispatch from Esther and Mordechai to the Jews of Persia — and spread flat on the reader’s table; this letter-fold is a distinctive feature of the Megillat Esther. Some scrolls are illuminated (decorated with miniature paintings); the great Sephardic illuminated Megillot are remarkable works of art.
Hearing the Megillah
The mitzvah on Purim is to hear every word of the Megillah read from a kosher scroll. Hence the importance of: (1) attending shul on both Purim night and Purim morning; (2) finding a competent reader; (3) refraining from talking during the reading; (4) ensuring that the noise made at Haman’s name does not drown out subsequent words. Failure to hear a word may require asking the reader to repeat it. A New Jew who does not yet know the trope can follow along with a printed Megillah.
Where Denominations Diverge
Universal in Orthodox practice for Esther on Purim, though customs for the other four megillot vary by rite: Ashkenazim generally read Shir HaShirim on Shabbat Chol HaMo’ed Pesach, while many Sephardim instead chant it before Minchah on the last day of Pesach (or weekly, before Shabbat). Conservative practice on Esther is essentially identical to Orthodox. Reform observance of Megillah readings is increasingly common, especially for Esther on Purim and Eichah on Tisha B’Av. Reform congregations sometimes substitute partial readings or selected passages.
Sources
Megillot themselves (Shir HaShirim, Rut, Eichah, Kohelet, Esther) within the Ketuvim.
Mishnah Megillah; Talmud Bavli, Megillah.
Rambam, Mishneh Torah, Hilchot Megillah.
Shulchan Aruch, Orach Chaim 686–697.
The Reading of the Megillah - Additional Guidelines and Insights on Megillah Reading — Chabad.org.
Reading the Megillah — Aish.
Can I Read Megillah to Myself? — Chabad.org.
When do we read the Song of Songs? — Chabad.org.
Further Reading
Adele Berlin, Esther (JPS Bible Commentary).
Rabbi Adin Steinsaltz, The Five Megillot.
Aviva Zornberg, The Beginning of Desire — for her Esther chapters.