Ingredients

5 pounds winter squash (such as butternut, buttercup, kabocha or hubbard), peeled, seeded and cut into 1-inch chunks (see Tip)
2 tablespoons extra-virgin olive oil, divided
1½ teaspoons salt
¼ teaspoon freshly ground pepper, divided
3 cloves garlic, minced
2 tablespoons chopped Italian parsley

Preparation

Preheat oven to 375°F.
Toss squash with 4 teaspoons oil, salt and ¼ teaspoon pepper. Spread evenly on a large baking sheet. Roast, stirring occasionally, until tender throughout and lightly browned, 30 to 45 minutes (depending on the variety of squash).
Heat the remaining 2 teaspoons oil in a small skillet over medium heat. Add garlic and cook, stirring, until fragrant but not brown, 30 seconds to 1 minute. Toss the roasted squash with the garlic and parsley. Taste, adjust the seasoning and serve.

Make Ahead Tip: Cut squash up to 1 day ahead; store airtight in the refrigerator.
Kitchen Tip: Make it easier to cut a pumpkin, acorn squash or other winter squash: pierce in several places with a fork; microwave on High for 45 to 60 seconds. Use a large sharp knife to cut in half. Remove the seeds and stringy fibers with a spoon.