Here is a challah trick that is applicable all across the sweet bread sphere: the moister, wetter and generally more difficult and sticky the bread dough, the more tender and cakey the bread will turn out. For challah and other egg and sugar-enriched doughs, this is exactly what you want.
My rule of thumb - only add enough flour for the dough to hold its shape. It should be a little sticky, but not unworkable. You should be able to knead it without it gluing itself to the counter (and your hands), but it shouldn't be bouncy and perfectly smooth, a little ragged around the edges is a good thing here. Add as little flour as you can bear and your challah will be all the softer for it.
Hope this helps and happy challah baking! And Happy New Year.
Oh and lest I forget, I have a recipe on Gilt Taste this week that is made for Rosh Hashanah - a honey glazed duck with apple and potato confit, so so good and I promise, it's really easy, not much hearder than roasting a chicken and so much more festive.

Thanks for the sweet bread tip. I've been wanting to make homemade challah for some time, and since I tend to focus on savory breads this is so helpful.
Posted by: art and lemons | 09/26/2011 at 10:08 AM
Also, I think if you refrigerate the dough for a little while it will be easier to braid, etc.--a big help when it's nice and sticky as you say! Dipping your hands in water periodically helps too. (I generally knead these doughs in the mixer though!)
Posted by: Sara | 09/26/2011 at 10:09 AM
Love this tip Melissa! Making challah at least twice this week so will put this into practice...
Posted by: Drwinnie | 09/26/2011 at 11:07 AM
Thanks for the great tip Sara! And happy challah making Winnie, let me know how it goes....
Posted by: Melissa | 09/27/2011 at 03:29 PM
I make challah every week and follow just the same principle! In fact, now that my daughters are old enough to pitch in with the braiding, I find I have to remind them not to add flour to the counter like we do when rolling other doughs. I leave the dough a bit on the wet side and the challah comes out moist and soft.
Posted by: Rivki Locker | 09/28/2011 at 08:19 AM
I find that my dough hook is my best friend with this type of dough. Really good advice as to just the degree of stickiness required. A little ragged round the edges is always a good thing in my book!
PS Came to your blog from the excellent interview by Dianne J.
Posted by: Sally - My Custard Pie | 09/29/2011 at 04:14 AM
Hi Melissa, I found your blog through Dianne J's site - and am so glad I did! I love the scrambled eggs + pesto + ricotta video on your site... I think that is going to be my dinner one day this week!
Also love the handy tips sprinkled through your blog - those are so valuable.
Posted by: Mel | 10/02/2011 at 03:38 AM
Great challah tips, thanks so much! I always get nervous when it's that sticky and end up adding more flour, resulting in a dryer challah. I need to break the cycle! :-) Shana Tovah!
Posted by: Katherine Martinelli | 10/02/2011 at 02:56 PM
I've wanted to try this ever since the episode of Sex And The City where Charlotte cooks a Jewish dinner for Harry. I'm definitely trying this sometime soon.
Posted by: Joana | 10/03/2011 at 10:18 AM
I miss challah french toast! I'm going to have to make some soon!
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Posted by: TranManuela31 | 10/07/2011 at 11:31 PM