While I enjoy trying new recipes, holidays and get togethers aren't the time when I experiment. There are too many people to feed and desserts to bring to gatherings for me to risk a new recipe that might potentially fail. I fall back on my tried and true recipes, not only because I know how they'll turn out but often people have had them before and that's what they request I make.
For Thanksgiving every year, I prefer to make a variety of desserts but not too much of each one. I serve them in individual-sized portions so people can sample what they want but not overeat themselves sick. Moderation is key, after all. Plus you want to leave them wanting more, not wishing they hadn't eaten themselves to gluttony :).
I don't necessarily have a typical dessert I make every year but I do rotate amongst a select few crowd pleasers. For those who don't want to search through my blog, here are the links to this year's dessert offerings:
Pumpkin Upside-Down Cake with caramelized pecans and cranberries (I never liked pumpkin or cranberries until I made this cake)
Apple Cobbler, aka Apple Crumble Bars that I made recently and that trumped my long-standing apple cobbler recipe. Every time we have a family get-together, I have to make cobbler as that's a family favorite.
Red Velvet Cupcakes - requested by my nieces, especially this particular recipe. Although I originally made it as a cake the first time, any cake adapts easily to the cupcake version. Just watch the baking time carefully as cupcakes will bake much faster than cakes since they're smaller. We're going to make the mini cupcake version which can bake/dry out very quickly so I'll be hovering over the oven while these are in there.