Using a large, sharp knife half the squash. To make this process easier, microwave the squash for 1-2 minutes to soften.
Scoop out the seeds and stingy membrane. Rub olive oil all over cavity and outer rim of the squash.
Add 1 tsp of butter to the inner cavity of both halves of squash. Sprinkle brown sugar evenly between the two halves of the squash. Sprinkle with salt and pepper to taste.
Bake for one hour or until tender. Squash should be very tender when pierced with a fork.