Prepare the squash: Preheat your oven to 400°F (200°C). Brush the cut sides of the acorn squash with 1 tablespoon olive oil and season with salt and pepper. Drizzle each half with maple syrup or sprinkle with brown sugar.
Roast the squash: Place the squash halves cut-side down on a baking sheet. Roast for 30-35 minutes, until the flesh is tender when pierced with a fork but still holds its shape. Flip them over during the last 5 minutes of cooking.
Prepare the filling base: While the squash roasts, heat the remaining 2 tablespoons of olive oil in a large skillet over medium heat. Add the diced onion and cook for 3-4 minutes until softened and translucent.
Add aromatics: Stir in the minced garlic and cook for another 30 seconds until fragrant, being careful not to let it brown or burn.
Wilt the spinach: If using fresh spinach, add it to the skillet in batches, stirring until each batch wilts before adding more. If using frozen spinach, add it to the skillet and stir to combine with the onion mixture.
Create the creamy texture: Reduce heat to medium-low and add the cream cheese, stirring until it melts completely. Pour in the heavy cream and cook for 2-3 minutes until the mixture thickens slightly.
Finish the filling: Stir in ¼ cup of Parmesan cheese and the nutmeg. Season with salt, pepper, and red pepper flakes if using. The filling should be creamy but not runny.
Stuff the squash: Spoon the creamed spinach mixture generously into each roasted squash half. Top with the remaining Parmesan cheese and panko breadcrumbs if using.
Brown the tops: Return the stuffed squash to the oven for 10-15 minutes, until the tops are golden brown and slightly crispy. For extra browning, broil for the last 1-2 minutes, watching carefully to prevent burning.
Serve: Allow the stuffed squash to cool slightly before serving. Each person can enjoy their own squash half as a main course, or halve them again for smaller side portions.