Preheat oven to 425 degree F. Drizzle 1 teaspoon of olive oil over each squash (or spray with olive oil cooking spray). Sprinkle with a bit of salt and pepper and place squash face side down on a baking sheet. Roast for 50 minutes-1 hour or until squash is fork tender. Remove and cool for 10 minutes.

Heat 1 teaspoon of olive oil or butter to a dutch oven or large saucepan over medium-high heat. Add apples, carrots, onions, and sauté for 10 minutes or until apples begin to cook and onions become translucent. Next add cinnamon and stir again. Remove from heat.

Once the squash is cool enough to handle, scoop out the roasted squash and add to the dutch oven. 

Next add the chicken broth and bring the mixture to a boil. Cover, reduce heat, and simmer for 20 minutes longer. Remove from heat and stir in milk, maple syrup, and a pinch of salt.

Place ½ of the squash mixture in a blender. Blend until smooth, and repeat with the other half of the mixture. Return to saucepan. 

Add chicken broth or water to thin to desired consistency. Adjust seasonings and season with salt and pepper. Serve with toast, or glaze with a bit of brown butter.