Preheat oven to 425F and move the rack to the top third of the oven. Line a baking sheet with parchment paper.
Cut the squash in half lengthwise and peel it. Scrape out the seeds.
Place the squash cut side down on the baking sheet. Coat with olive oil and salt & pepper. Roast for 15 minutes.
Add 2 tbsp of the honey and the cinnamon to a small bowl.
Take it out of the oven and let it cool for a couple of minutes. Cut the squash crosswise, going slowly so that you don't cut all the way through. Brush the honey/cinnamon mixture onto the squash, getting it into some of the crevices.
Return the squash to the oven and roast for an additional 45 minutes or until it's tender, browned, and cooked through. Take it out of the oven and brush on an additional tablespoon of honey. Serve immediately.