Preheat your oven to 425°F (220°C). Position the oven rack to the top third to ensure even cooking. Line a baking sheet with parchment paper, which makes cleanup a breeze.
Prepare your butternut squash by cutting it in half lengthwise. Use a vegetable peeler to remove the skin, then scoop out the seeds with a spoon. Take your time during this process to ensure a smooth surface for roasting.
Place the squash cut-side down on the prepared baking sheet. Drizzle with olive oil and sprinkle generously with salt and pepper. Make sure every inch is coated to enhance the flavors.
Roast the squash in the preheated oven for about 15 minutes. This initial roasting will start to soften the squash and bring out its natural sweetness.
While the squash is roasting, mix together honey and ground cinnamon in a small bowl. This mixture will create a delicious glaze that infuses into the squash.
After 15 minutes, take the squash out of the oven and let it cool for a few minutes. Carefully cut crosswise into the squash, ensuring not to cut all the way through. This step allows for better caramelization and flavor absorption.
Brush the honey and cinnamon mixture generously over the cut surfaces of the squash, letting it seep into the crevices for maximum flavor.
Return the squash to the oven and roast for an additional 45 minutes, or until it is tender, browned, and cooked through. You’ll know it’s done when a fork easily pierces the flesh.
Once roasted, remove the squash from the oven and brush on an additional tablespoon of honey for that extra touch of sweetness.
Serve the Honey Cinnamon Roasted Hasselback Butternut Squash immediately, garnished with fresh herbs if desired. Enjoy the warm, comforting flavors of fall!
