When winter squash shows up in farmers’ markets and produce stands in the late days of summer, it’s a signal to start the inevitable seasonal transition. It can be hard to give up summer tomatoes and corn and make a sharp U-turn toward cool-weather cooking. Thank goodness for all the different colors, shapes and sizes winter squash come in—it keeps things interesting. For a cheffy touch, try drizzling the squash with a tiny bit of aged balsamic vinegar when it comes out of the oven.–Karen Tedesco

david caricature

Why Our Testers Loved This

Our testers loved the ease of preparation for this one-pan dish, the tender caramelized shallots, and that it elevated a simple, classic side dish to a noteworthy part of their meal.

Notes on Ingredients

  • Squash–Any winter squash will work here, and you can peel it, but it’s not necessary. The peel on acorn and delicata squash becomes very tender during roasting.
  • Shallots–You can substitute half a red onion for the shallots. Slice it into thin wedges.
  • Aged balsamic vinegar–A drizzle of good-quality vinegar really elevates the dish. It’s optional but highly recommended.

How to Make This Recipe

  1. Prepare the squash. Preheat the oven to 425°F. While it’s heating, toss the squash and shallots with oil and salt on a baking sheet.
  2. Roast the squash. Cook until the squash is tender and the shallots are caramelized, stirring once during roasting.
  3. Finish the dish. Sprinkle the parsley and crushed red pepper over the roasted winter squash and shallots and drizzle with vinegar, if using.

Recipe FAQs

What kind of winter squash should I use?

You can make this with a combo of squash varieties of just one type. You don’t really need to peel the skin off acorn or delicata squash—it gets tender when cooked, and it helps keep the squash in shape. You can use this approach with almost any type of winter squash, including butternut squash.

What should I serve with this?

This would be lovely as part of a classic roast chicken dinner, or served alongside a roasted and braised turkey. If you’d like to serve it as part of a vegetarian meal, try serving it with this greens and grains soup.

Helpful Tips

  • Don’t crowd your baking sheet as the squash will end up steaming instead of roasting. If it seems too full, divide the squash and shallots between two rimmed baking sheets.
  • This recipe is suitable for gluten-free, dairy-free, vegan, and vegetarian diets.
  • Leftovers can be stored in a sealed container in the fridge for up to 4 days. To make use of leftovers, use the squash in this roasted delicata squash and kale salad, or add it to grain bowls.

More Great Roasted Squash Recipes

Write a Review

If you make this recipe, or any dish on LC, consider leaving a review, a star rating, and your best photo in the comments below. I love hearing from you.–David

A white oval platter topped with roast winter squash and shallots.

Roasted Winter Squash and Shallots

5 / 2 votes
This roasted winter squash and shallots is proof that good food doesn’t need to be complicated. Here, acorn squash and shallots are roasted until tender and finished with parsley, red pepper flakes, and a little balsamic vinegar.
David Leite
Servings4 servings
Calories290 kcal
Prep Time15 minutes
Cook Time40 minutes
Total Time55 minutes


  • 3 pounds acorn, delicata or kabocha winter squash, seeded, peeled, if desired, and cut into 1-by-3–inch (2.5-by-8–cm) pieces
  • 3 or 4 medium (6 oz) shallots, halved lengthwise and each half quartered in wedges
  • 1/4 cup extra virgin olive oil
  • 1 teaspoon kosher salt
  • 1/2 cup fresh Italian parsley leaves
  • Crushed red pepper, to taste
  • Aged balsamic vinegar (optional)


  • Preheat the oven to 425°F (220°C).
  • On a large rimmed baking sheet, arrange the squash and shallots in a single layer. Drizzle with the oil, sprinkle with the salt and toss to combine.

    ☞ TESTER TIP: You don’t want your squash to be crowded. If there’s not enough room to arrange everything in a single layer on the baking sheet, divide the squash and shallot mixture between two baking sheets.

  • Roast until the squash is tender and deep golden brown on the edges, stirring once during cooking, about 40 minutes.
  • Scatter the parsley over the vegetables, and sprinkle them with the crushed red pepper and a drizzle of balsamic vinegar, if using. Serve immediately.


  1. Storage–Leftovers can be stored in a sealed container in the fridge for up to 4 days. Cube leftover squash and add to salads or grain bowls.
  2. Dietary–This recipe is suitable for gluten-free, dairy-free, vegan, and vegetarian diets.

Adapted From

Family Style

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Serving: 1 portionCalories: 290 kcalCarbohydrates: 43 gProtein: 4 gFat: 14 gSaturated Fat: 2 gPolyunsaturated Fat: 2 gMonounsaturated Fat: 10 gSodium: 601 mgPotassium: 1368 mgFiber: 7 gSugar: 4 gVitamin A: 1882 IUVitamin C: 51 mgCalcium: 139 mgIron: 3 mg

Nutrition information is automatically calculated, so should only be used as an approximation.

Tried this recipe?Mention @leitesculinaria or tag #leitesculinaria!
Recipe © 2020 Karen Tedesco. Photo © 2020 Karen Tedesco. All rights reserved.

Recipe Testers’ Reviews

This is such a basic roasting recipe that I have to admit to wondering why it was in the testing line-up. That said, after making it and beholding the beauty of the golden squash, the burnished shallots and the bright spark of color from the parsley and red pepper flakes, I appreciated it’s classic-but-better approach to a very simple dish. The recipe itself takes less than 10 minutes to pull together and then the magic of a high-heat oven takes care of the rest.

I’ve never roasted squash in its peel before and was pleasantly surprised to discover how tender and completely edible it became during roasting. The golden acorn squash was truly beautiful once roasted, and who doesn’t swoon for well-roasted shallots, soft and unctuous and full of umami?! The final garnishes of parsley and red pepper flakes may seem optional and superfluous, but this little ‘something extra’ really makes the dish special and party-worthy, too.

I followed the author’s brilliant suggestion to drizzle some aged balsamic vinegar over the finished dish and it elevated both the flavors and appearance; I hope that little morsel of wisdom works its way into the main recipe!

Wonderfully simple preparation that allows the ingredients to shine. Those of us without dishwashers will also appreciate that you mix the ingredients together in the baking sheet!

I didn’t have shallots on hand, so I used half of a red onion, which caramelized nicely alongside the olive oil-coated acorn squash. The squash was tender after 30 minutes, but lightly browned and more flavorful after 40 minutes.

The parsley and pepper flakes add a pop of color and zing to the warm and comforting squash. It’s a versatile side dish to any meal or cuisine; I’ve served it on a mixed greens salad, a whole grain salad, and with roasted chicken.

We had four delicata squash on hand and jumped at this roasted winter squash recipe—preparing the ingredients took less than 10 minutes. Our oven runs hot, so we gave the vegetables a good stir and turned the pan at 15 minutes, with everything perfectly cooked after 25 minutes.

The dish received universal rave reviews (the shallots are caramelly wonderfulness) and easily served six. This was so delicious and simple we definitely will make again—the only two possible changes we’ll consider are reducing the salt just a bit, and doubling everything to have plenty on hand for the next meal.

About David Leite

David Leite has received three James Beard Awards for his writing as well as for Leite’s Culinaria. His work has appeared in The New York Times, Martha Stewart Living, Saveur, Bon Appétit, Gourmet, Food & Wine, Yankee, Los Angeles Times, Chicago Tribune, The Washington Post, and more.

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