Katy, I'm so glad you need the help, because I LOVE this topic. I've been hosting Thanksgiving for nine years (one off year) and I like to think I get a little better at it each time and also enjoy it more the more organized I am. The first year, we were in an apartment and I was early in my pregnancy with Tank. I kept having to go lie down and feeling like I was going to throw up! Now that's a happy family memory.
Okay, let's get going. Next step is menu planning. Each year, I put together what I like to call my Thanksgiving cookbook. I take a sheet of paper and write the menu on it. If I am using recipes, I make photocopies of them and staple them to the menu in the order I am going to need them. This is not the time when you want eighteen cookbooks sprawled on your counter getting crap all over them or random recipes cut out of magazines getting lost. I don't make the same meal every year. I like to switch it up. I also tuck the cookbook away and next year I can look and see what I did and how I did it.
Before I make my shopping list, I figure out everything I can make ahead and write down the order. For example, I will make cranberry sauce on Monday. Tuesday, the house is being cleaned, mashed potatoes and setting the table on Wednesday, etc. It can also be a good idea to factor in things on a countdown list that are not food related, like do you have guests arriving Wednesday night? When are you going to make up beds for them? What are you going to serve them for dinner on Wednesday? Do you have stuff for their breakfast? When in the process will you have help and what tasks are you willing to parse out. Will you need to buy ice to have enough? Do you have a place to store it so you can buy it in advance? Do you need to allow time for dough to rise? Will you make a signature cocktail or have wines? Beverages are not something I care much about, so I'm happy to outsource that to a guest and my husband to coordinate. Also, we usually have my in-laws on Wednesday night and I've been cooking all day, so traditionally we get Chinese or Thai takeout.
It's also helpful to work backwards. What time are you serving dinner? 2pm? 4pm? I am not a fan of the super mega early dinner. I'm a 4pm gal. But this is an important piece of information to nail down. I like to tell guests to start arriving around noon. I have noshes out, they watch football on tv, they might go in the backyard and play a little football (okay, this is my Kennedy family Thanksgiving fantasy where my rugged boys with their mussed hair and ski chiseled features are getting all ruddy faced playing touch football in rugby shirts on a sunny Thanksgiving afternoon...but I digress) (although I did just manage to use rugged, ruddy and rugby all in one run-on sentence).
Once you decide on the menu, are you going to ask anyone to bring anything? Despite my previous post, I think Thanksgiving can be a potluck-y holiday and many people want to bring something. It can also be a very expensive holiday and everyone knows this. Are you just going to ask them to bring sweet potatoes or are you going to give them a specific recipe you want them to use? You can ask someone who doesn't cook to bring bread or rolls or pretty paper napkins for dessert. I ask people to bring the following things:
beverages: alcoholic and non (sister in law)
cheese and crackers (sister in law)
pastries and fruit for Friday morning (my mother in law)
pie (my mom)
Other than that, I prefer to do it myself.
Okay, now take the back of your cookbook and start writing your shopping list. I will go to the store more than once, but I try to keep it to two trips, maybe three. The first is the trip to Fred Meyer. and it will happen in the next day or two. I need pecans and FM sells them in bulk, so I think they are fresher and cheaper and I can get them ahead of time. That's the kind of thing I am buying now. However, I won't buy salad stuff and the like until Tuesday and I will buy it at QFC where I think the product is better. Look at your shopping list and the order you need to make things. Think about what you want to get at which stores. Think about when your grocery store circular comes out. Then, using all that information, divide your list into the trips. At this point, I've already purchased things like flour and butter and the jelly I use in my cranberry sauce. Shelf stable pantry items and frozen foods are good to stock up on a few weeks out as it helps distribute the cost and your brain.
I personally refuse to go to the store on Wednesday. Every grocery store in America will be a complete madhouse. I will do my final shopping on Tuesday and Wednesday is reserved for cooking and setting the table.
I have more on this subject and may get to it later today...questions?