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Preheat oven to 400°F. Line a large pan with parchment paper.
Cut acorn squash in half lengthwise and scoop out the 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.
Once done, 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.