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Preheat oven to 400°F. Line a baking pan with a sheet of parchment paper.
Cut the acorn squash lengthwise and scrape out the pulp and seeds.
Brush squash with olive oil and season with salt and pepper. Place face down in a baking dish and cook for 15 minutes.
While the squash is cooking, melt the butter, honey, and cinnamon in the microwave in a microwave-safe bowl.
Remove the squash from the oven and flip them over, brushing them with the butter mixture and cooking for another 15 minutes.
Garnish with fresh herbs if desired.