Preheat your oven to 375°F (190°C).

Halve the acorn squash and scoop out the seeds. Brush cut sides with olive oil and sprinkle with salt and pepper.

Place the squash halves cut side down on a baking sheet. Bake for 25-30 minutes, until tender.

Melt the butter in a medium pan over medium heat. Add diced apples, walnuts, and cranberries; cook for 5-7 minutes.

Add cinnamon, nutmeg, brown sugar, and salt. Stir and continue to cook for another 2-3 minutes.

Remove the squash from the oven, turn them cut side up, and fill with the apple mixture.

Drizzle maple syrup over each stuffed squash half.

Return to the oven and bake for an additional 15-20 minutes until completely tender.

Let cool for a few minutes before serving to meld the flavors.