My favorite thing to do with a winter squash is to stuff it.
The browned butter and roasted vegetables make this special, but roasting everything in the oven at once makes it easy to prepare.
This is a classic dump-and-cook crock pot recipe.
Pie does not get better than this. Reducing and concentrating the juices of the apples make it necessary to use only about half the usual amount of thickener, resulting in a purer apple flavor, a juicy filling, and a crisp bottom crust. Make apple pie in the fall, at the height of the apple season, or whenever you have the yearning.
A press-in crust, short bake time, and do-ahead option liberate you (and your oven) on Thanksgiving Day.