More will be added as time permits.
Beginning Anew: A Woman’s Companion to the High Holidays. Gail Twersky Reimer and Judith A. Kates, editors. Simon and Schuster, 1997.
Days of Awe: A Treasury of Jewish Wisdom for Reflection, Repentance, and Renewal on the High Holy Days. S.Y Agnon, editor. With forward by Arthur Green. NY: Schocken, 1995. (originally published in 1948).
Companion to the High Holydays Prayer Book. Ha’rav Lord Jakobivits. London: Vallentine Mitchell, 2002.
Rosh Hashanah Readings: Information, Inspiration, Contemplation. . Rabbi Dov Peretz Elkins, editor. Woodstock, VT: JewishLights, 2006.
Yom Kippur Readings: Information, Inspiration, Contemplation. . Rabbi Dov Peretz Elkins, editor. Woodstock, VT: JewishLights, 2005.
Joseph Rosenstein, editor/translator of Siddur Eit Ratzon, offers a free meditation on Psalm 27 for Elul as well as other resources. See also Machzor Eit Ratzon.
For those working with young people in homeschooling or Hebrew school settings, the 4th “honor” level volume in “The New Siddur Program for Hebrew and Heritage” is a useful resource. Consumable workbook style book assuming basic siddur Hebrew and concentrating on both language and high holiday themes. West Orange, NJ: Behrman House, 1994.