Rosh Hashanah is one of those holidays where I host large crowds, usually 20-30 people so I often start baking challahs in August. I make at least 16 large round loaves and dozens of rolls. As I write this, it is the first week of September and clearly I am behind in my schedule as I am still baking challahs for Shabbat each week. Good thing Rosh Hashanah comes later this year.
In addition to baking your challahs in advance, you can get a head start on other preparations if you also bake cookies and cakes in advance and freeze them. Apple desserts are better baked two days before the holiday to avoid them getting too mushy while thawing. Finally, soups and brisket can be made weeks in advance and frozen.
When I host a large crowd, I find that it takes forever to pass the challah, apples, and honey after the blessings, so now I give each person a plate with their own challah roll, a small dish of honey and cut apples. For my last cookbook, The Holiday Kosher Baker (Sterling 20113), I even invented apple and honey challah rolls, which further streamlines the whole process. The plates make a pretty table decoration as well.
This year my meals will feature these flavored challah rolls. Two are savory and one is sweet. You only have to prepare one challah dough and use it to make three roll variations. In my effort to move towards healthier breads and desserts, I added some white whole-wheat flour to the dough. You can always substitute more bread flour for a more traditional taste. Freeze each type of roll separately by wrapping the 8 rolls in foil. Reheat, wrapped in foil, at 325°F for about 25-30 minutes and the rolls will taste like you just baked them. Shana tovah.