This is a great dish as the weather begins cool off. It uses some great fall flavors of warm spices, along with apples and winter squash.
Sprinkle each of the squashes with a tablespoon each of the ginger, cinnamon, and nutmeg. Then season with salt and pepper to taste. Reassemble the 2 halves of two squashes (sans seeds) and wrap each one tightly in aluminum foil. Place on a foil lined sheet pan and roast at 350°F until it a knife pierces it easily, about 90 minutes.
While the squash roasts, add the oil to the skillet and place over medium heat. Add the leeks to the pan and season with salt and pepper. Cook, stirring frequently until the leeks just begin to brown, then add the apples and dates as well as the remaining cinnamon, ginger, and nutmeg. Continue to cook and stir until the apples are a caramel brown and remove from the heat.
Cut each squash in half the short way. You should have 8 shorter pieces when you are done. Fill each squash piece with the apple, leek, and date mixture and serve.