Acorn squash pairs well with foods made with fall herbs like rosemary, sage, thyme, and bay leaf, as well as warm spices like cinnamon, cloves, nutmeg, and ginger. Acorn squash also goes well with all the traditional holiday mains: turkey, ham, prime rib. It fills out an easy weekday meal nicely, too. Try it with roast chicken, Brussels sprouts, or mushroom soup.