Roasted Winter Squash
Roasted winter squash
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4.0 (4 rated)

This is one of those colorful, delicious side dishes that hits my table in October and stays there through the winter months. It's seasonal and delicious and easy to make. By roasting the squash it is transformed. It becomes the centerpiece rather than a side dish.


  • Orange sauce (makes about 1 cup)

    • 3-4 medium oranges
    • 1½ cups leeks, cut into 1-inch pieces
    • 1 cinnamon stick
    • 1 cup water
    • 3 tablespoons butter, softened
  • Squash

    • 3 pounds winter squash, such as butternut, buttercup or acorn
    • 3 tablespoons extra-virgin olive oil
    • 1/2 teaspoon salt
    • 2-3 tablespoons butter, for the baking sheet
  • To serve

    • 1/2 cup orange sauce
    • 1-2 tablespoons balsamic reduction, homemade or store bought, for drizzling


For the orange sauce:

1. Rinse and dry the oranges. With a sharp vegetable peeler or paring knife, remove the outer peel of three of the oranges, in strips. Don't take off any of the bitter white pith — if you do, trim it away from the strip. Put the strips of peel in a small saucepan.

2. Cut the oranges in half and squeeze to get out all the juice: You should have a bit more than a cup. (Juice another orange if you have a cup or less.) Add the juice to the saucepan along with the leek pieces, cinnamon stick and water. Place the pan over high heat and bring to a boil. Reduce the heat to maintain a perking boil and let the sauce cook for about 30 minutes, reducing to about 1/3 of the original volume.

3. Pour the sauce into a sieve set over a bowl. Remove the cinnamon stick and the pieces of peel (wiping them off and saving any juices) then press and scrape the leek pieces with a spoon or spatula to retrieve as much liquid as you can.

4. You should have about 3/4 of a cup of orange "soup." To thicken this into a sauce, whisk the butter into it bit by bit.

5. Serve the sauce hot. Reheat on the stovetop if necessary and whisk until smooth.

For the squash:

1. Preheat the oven to 400°F.

2. Cut the squash in half through the stem and blossom ends. Scoop out all the seeds and fibers so the flesh is clean.

3. Place each half cut side down and, with a sharp knife, cut straight across to trim the ends of the squash. Then cut the squash into even slices (cutting cross-wise) or wedges (cutting lengthwise), about 2-inches thick at the widest part.

4. Remove the peel from the squash slices with a sharp vegetable peeler or paring knife. (With acorn squash, strip off the peel just from the top of the ridges; this will help the pieces cook faster and creates a decorative striped look.)

5. Pile the squash in a mixing bowl, drizzle the oil and sprinkle the salt over the pile and toss to coat the slices with the seasonings.

6. Spread the butter on a large baking sheet (or line it with a non-stick silicon sheet.). Lay the slices flat on the sheet with plenty of space between them for even caramelization.

7. Bake about 20 minutes then flip the pieces over; bake for another 20 to 25 minutes, until they are tender all the way through (poke with a fork to check) and nicely caramelized on the edges.

To serve:

Serve hot, piling up the squash pieces on top of a pool of orange sauce; drizzle balsamic reduction in thin streaks all over the top. The squash is also delicious with just one of the sauces or with only a final drizzle of good olive oil and another sprinkle of salt before serving by itself!