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Place a rack in the center of your oven and preheat the oven to 350 degrees F. For easy clean up, line a rimmed baking sheet with parchment paper or aluminum foil.
Wash and dry the squash. Trim off the top and bottom ends, then carefully slice it in half lengthwise. (No need to peel it.) Scoop out the seeds. Place it cut-side up on the prepared baking sheet.
Brush the cut sides of the squash with 1 tablespoon of the olive oil and the maple syrup. Sprinkle with 1/2 teaspoon salt and 1/4 teaspoon black pepper. Bake for 1 hour 15 minutes, or longer depending upon the size of your squash, until very tender and the squash pierces easily with a fork. Let rest until cool enough to handle.
Carefully scoop out the flesh and place it in the bowl of a stand mixer or a large mixing bowl. Add the nutmeg, cayenne, milk, Parmesan, parsley, and remaining 1 tablespoon olive oil, 1/2 teaspoon salt, and 1/4 teaspoon black pepper. Mash the butternut squash, either by hand with a potato mixer, or with an electric hand mixer on low speed, or the paddle attachment of a stand mixer on low speed, until it is as smooth as you like (we leave ours a bit chunky). Taste and adjust the seasoning as you like. Enjoy hot.