Something I can encourage, however, is squash for breakfast in the form of a smoothie that tastes like pumpkin pie. The resulting drink sips like the more responsible cousin of a pumpkin pie milkshake. You can make this smoothie with any variety of winter squash (or even a sweet potato if you're a SP pie loyalist). Roasting concentrates the flavor and caramelizes the cut surface of the squash, which is essential for giving your smoothie the sweet, cooked flavor of pie. of cold roasted squash (that's about a quarter of an acorn squash, depending on size; about 2 to 2½ cups cubed) into your blender for every two servings.