What I like to do, particularly with the holidays is think about what flavors I associate with that holiday, and then go looking for recipes using that flavor (which I find less daunting than searching out just "any" recipe). I also like to take a look at the farmers market and see what is in season rather than trying to use out of season (and expensive) produce.
That has led to family favorites like cranberry salsa, cranberry baked brie, cranberry fritters, persimmon steamed pudding, pumpkin bread pudding, mashed potato and sweet potato with roasted garlic and parmesan, roasted parsnips with horseradish butter, butternut ravioli with broccoli rabe and browned butter, cream of chestnut soup, etc.
With a beef roast, I highly recommend roasted parsnips with horseradish butter
. These were fabulous. I did not add all the butter to the parsnips, but just added it to taste, and we gobbled them up (and neither of us cares for horseradish normally). We also like roasted brussel sprouts tossed while hot with blue cheese and toasted pecans.
Personally I'd also go for a soup. Curried pumpkin, or butternut with blue cheese are the ones I'm considering (although cream of chestnut is also a possibility).
And then I also like to have a cold veggie dish and a bread (biscuit or rolls) dish. For Thanksgiving this year I served a fennel apple salad with blue cheese that was excellent, but in years past it's been a plain green salad with apples, cheese, nuts and a cranberry vinaigrette. Around here bread is usually angel biscuits, which have the flakiness of a biscuit with the yeast flavor of a roll.