Preheat your oven to 400 degrees. Line a baking sheet with parchment paper and set aside.
Cut the squash in half lengthwise, then scoop out the seeds and discard them. Drizzle with a bit of olive oil then place the squash halves, cut side down, on the baking sheet.
Roast the butternut squash in the oven for 50 minutes, or until it is tender and easily pierced with a fork.
Remove the squash from the oven. Once cool enough to handle, scoop out the flesh into a large mixing bowl, discarding the skin.
Add the butter, maple syrup, milk, cinnamon and nutmeg to the squash and mash until smooth using a potato masher or an electric mixer. Add salt and pepper to taste if desired and serve.
Cut safely: Use a sharp chef’s knife and cut carefully through the squash. If it’s too tough, microwave it whole for 2–3 minutes to soften slightly before slicing.
Roast face down: Placing the squash halves cut side down on the baking sheet helps them cook evenly and caramelize.
Check doneness: Squash is ready when a fork slides easily into the thickest part. Larger squash may take up to 60 minutes.
Texture preference: For a rustic mash, use a potato masher; for ultra-smooth results, use a hand mixer or food processor.
Adjust sweetness: Taste before serving, add a touch more maple syrup if you prefer it sweeter, or leave it out entirely for a savory version.
Flavor variations: Stir in cinnamon, nutmeg, or fresh herbs like thyme for a seasonal twist.
Serving ideas: Perfect alongside roasted turkey, chicken, or pork, or served in a vegetarian grain bowl.