1. Preheat oven to 400°.
2. Place the squash halves face up on a baking sheet. Sprinkle with salt, pepper, and dark brown sugar. Take a pat of butter and break it into pieces and put on 1 half of the squash. Repeat another pat of butter on the other half.
3. Roast squash for approximately 30-45 minutes. Squash is done when you can easily poke the tip of a knife through it. It should feel soft and not give the knife any resistance.
4. Let squash cool to the touch and then scoop out the squash away from the skin with a large spoon. You can mash it at this point or you can store it in a plastic container in the fridge until the next day.

The Mashing

1. Microwave the squash until hot.
2. Add 1 1/2 tablespoons butter, cream, cinnamon, maple syrup, garlic, and 1/2 teaspoon salt. Mix together with an electric hand mixer or hand mash together until creamy. Add additional salt or butter to taste.
3. Store up to 2 days in refrigerator.