Preheat the oven to 400°F (200°C) and line a rimmed baking sheet with parchment paper.
Slice each honeynut squash in half lengthwise from stem to base using a sharp chef's knife.
Use a metal spoon to scrape out and discard the seeds and fibrous pulp from the cavity of each squash half.
In a small bowl, whisk together the olive oil, maple syrup, salt, pepper, and cinnamon.
Place the squash halves on the prepared baking sheet, flesh-side up.
Brush the oil and spice mixture evenly over the exposed flesh of each squash half.
Roast in the center of the oven for 25 to 30 minutes, or until the flesh is easily pierced with a fork and the edges have begun to caramelize.
Remove from the oven and allow to rest for 5 minutes before serving.