On average, one pound of raw squash will yield one cup of cooked and mashed squash. Scale the recipe down, if you like.

4 lbs winter squash; or 4 c cooked, mashed squash
2 cloves garlic, finely minced; or 1/2 t garlic powder, or to taste
1 1/2 c milk
3 T extra-virgin olive oil
2 apples, cored and diced
salt and pepper, to taste

1. Cook squash, if necessary, according to your preference, then mash or purée, depending on what kind of texture you like. Place in a serving bowl.

2. Put minced garlic or garlic powder into a saucepan with the milk and heat  just to warm through. Add to squash purée along with olive oil and mix to combine. Fold in diced apples and season with salt and pepper. Serve.