Preheat the oven to 400°F (200°C). Line a baking sheet with parchment paper for easy cleanup.
Wash the acorn squash and cut 1 inch off the stem. Place the squash cut side down on a cutting board and slice it in half from top to bottom.
Using a spoon, remove the seeds and stringy pulp from the center of each half.
Use a sharp knife to cut crisscross lines into the flesh, being careful not to cut through the skin. This helps the butter absorb better.
Rub the cut sides with softened butter to coat, then sprinkle with brown sugar and cinnamon.
Place the squash halves cut side up on the prepared baking sheet. Roast in the preheated oven for 55-60 minutes, or until the flesh is fork-tender.
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Notes
For slices, instead of leaving the squash as halves, you can slice 1/2-inch thick. Melt your butter to drizzle it on, then season. Roasting time will be reduced to 30-35 minutes.
For savory, replace brown sugar and cinnamon with 1/2 teaspoon salt and 1/2 teaspoon black pepper. You can also add any of the following options for extra flavor: