Winter Squash Bowl
- 1 medium butternut squash (about 1½ lb.)
- 5 small winter squash (about 1 lb. each; such as acorn, carnival, delicata, sweet dumpling, or sugar pumpkins), divided
- 4½ teaspoons olive oil, divided
- 3 teaspoons pure maple syrup (optional), divided
- Kosher salt and freshly ground black pepper
- 1 tablespoon unsalted butter, room temperature
- 1 teaspoon fresh thyme leaves
- Preheat oven to 400°. Line 2 rimmed baking sheets with parchment paper. Cut butternut squash in half crosswise. Set top half aside. Remove seeds and strings from bottom half; discard. Place bottom half of squash on 1 baking sheet. Remove caps from 3 of the small squash by cutting a circle 1″ around stems with a small serrated knife (as for pumpkin carving). Slice off and discard strings from bottom side of caps. Scoop seeds and strings from centers; discard. (If using delicata or other oblong squash, cut in half crosswise and scoop out seeds and strings.)
- Cut a thin slice off the bottom of each of the 3 hollowed-out small squash so squash sit evenly on a flat surface; place (with caps on) on baking sheet along with bottom of butternut squash. Drizzle insides with ¼ tsp. olive oil and ¼ tsp. maple syrup (if using). Season cavities with salt and pepper. Bake until a paring knife inserted into squash meets no resistance, about 1 hour.
- Meanwhile, remove stems from remaining 2 small squash and cut squash in half lengthwise. Remove seeds and strings from small squash and top half of butternut squash; discard. Peel and chop squash into ¼” pieces; place in a large bowl. Add remaining 4¼ tsp. oil and toss to coat. Season with salt and pepper. Spread in a single layer on remaining sheet and bake, stirring once, until squash is tender, about 30 minutes. Transfer to a large bowl and toss with remaining 2¾ tsp. maple syrup (if using), butter, and thyme. Divide among hollowed-out butternut and small squash and serve warm or at room temperature.