Preheat the oven to 425°F and line a large baking sheet with parchment paper.

Cut the bacon into thin lardons. Cook in a skillet over medium-high heat until almost crisp. Move the bacon to a plate and keep the grease.

Toss the squash with the bacon grease, salt, and pepper. Spread it in an even layer on the baking sheet and roast for 25 minutes.

While the squash roasts, stir the maple syrup and bourbon together in a small bowl.

Take the pan out of the oven and scatter the bacon over the squash. Pour the maple bourbon mixture over everything, stir to coat, and spread it back into one layer.

Roast for another 10 to 15 minutes, until the bacon is crisp and the squash is browned at the edges. Start checking at 10 minutes so the glaze doesn’t burn.