Preheat your oven to 400°F (200°C).
Cut the acorn squashes in half and scoop out the seeds.
Drizzle olive oil over the flesh of each half.
Season with salt, pepper, and cinnamon.
Place the squashes cut-side down on a baking sheet.
Roast in the preheated oven for 25 minutes.
Meanwhile, mix brown sugar, walnuts, and cranberries in a bowl.
Remove the squashes from the oven and flip them over.
Fill each half with the walnut mixture.
Drizzle maple syrup over the top and return to the oven for another 20 minutes.