Preheat your oven to 375°F (190°C).

Brush the cut sides of each acorn squash half with olive oil, then sprinkle with salt and pepper.

Place the seasoned squash halves cut side down on a baking sheet. Bake for about 25-30 minutes.

Melt the unsalted butter in a skillet over medium heat and add the diced apples, walnuts, and cranberries. Sauté for about 5-7 minutes.

Stir in the cinnamon, nutmeg, brown sugar, and salt. Cook for another 2-3 minutes.

Flip the squash cut side up and pack the apple mixture into each half.

Drizzle maple syrup over the tops of the stuffed squash.

Bake for an additional 15-20 minutes until tender and lightly browned.

Let the squash cool for a few minutes before serving.