How to Roast Any Squash and Ace Your Meal Prep

Updated 10/24/19

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For me, one of the most exciting things that comes with the changing of the seasons is the slew of new produce. While the spring and summer months are praised for the assortment of crisp, green, vibrant veg they bring, fall and winter offer up a heartier lot in the form of crunchy bulbs of fennel, deep burgundy, stain-everything-in-sight beets, and a sundry selection of squashes.

I happen to be a fan of all three of these vegetables, but squash is hands down one of my favorites—especially when it comes to things like meal prep because I can buy one large squash, roast it on a Sunday, and use it in multiple different dishes throughout the week. From acorn to kabocha, butternut to delicata, here’s how to roast (and use up) all your favorite winter squashes.

How to Roast a Whole Squash

One of the hardest things about roasting a squash starts at the cutting board. Squashes are notoriously difficult to cut in half, peel, and generally deal with because they’re hard-fleshed and their large, odd, and often bulbous shapes make them unwieldy—not a fun thing when you’re swinging around a sharp chef’s knife. However, there is a method in which you can skip that step altogether and roast the squash into something sweet, soft, and super easy to work with—brilliant, right?

To roast a whole squash, use a sharp knife to make many small, relatively deep incisions all over the squash. These holes will allow hot steam from the inside of the squash to escape as it roasts. This is a very important thing because, similar to a potato, if a squash is left whole and hole-less, the pressure from the steam could cause it to explode—both a safety hazard and an entirely avoidable nuisance.

Transfer the pierced squash to a nonstick, parchment paper-, or aluminum foil-lined baking sheet and bake in a preheated oven at 375°F.

Depending on its size, it could take anywhere between 40 minutes to 2 hours to reach the ideal, fork tender texture.

I would check it about 40 minutes in by slipping a fork into the flesh, it should go in easily, with little to no pressure—but if not, continue roasting and check it again every 15 to 20 minutes after that until it’s fork tender.

Let the squash cool for at least 30 minutes before halving it lengthwise. Scoop out the seeds and stringy core, then slice it up and serve simply with generous pats of butter, salt, and pepper or remove the peel completely, mash up or purée the flesh, and use it in soups, as a ravioli filling, in a sauce, as a side dish, or even in a sweet or savory baked good. 

How to Roast a Halved Squash

Like I said above, it’s not an easy task to halve most squashes, even with the sharpest of knives, and unfortunately, there’s no foolproof trick to make it easier. Basically, the best thing you can do is choose your biggest, sharpest knife, and use caution. I like to give the squash a gentle thwack almost like I would an avocado pit (keeping the squash on the cutting board, not in the palm of my hand—of course), then place my non-knife wielding hand on top of the knife and use my body weight as leverage to slowly wobble the knife through the squash. That being said, the best way is probably the way you’re most comfortable with, so you do you and it will (probably) be okay.

Once your squash is halved lengthwise, you can scoop the seeds and stringy core now, or you can simply leave them in and remove after roasting—the choice is yours.

Some say that leaving the seeds and core in while roasting adds extra flavor, but I’m not sold and personally tend to core all my squashes before roasting.

After coring (or not), rub the cut side of the squash with some olive oil and season with salt and pepper. You can also sprinkle on some brown sugar, drizzle with maple syrup, or lightly dust on your favorite ground spice—cinnamon, cumin, or Moroccan ras el hanout all work well. Place the squash on a nonstick, parchment paper-, or aluminum foil-lined baking sheet. I prefer to roast them cut-side down because I like the brown, caramelized bits that come from that flesh to pan contact, plus I think it just makes the whole squash taste more squashy and have a better texture, but a lot of people roast them cut-side up. In the end it doesn't really make a huge difference, so experiment with both to see which you prefer.

Bake in a preheated oven at 375–400°F until the flesh is fork tender, as in the whole roasted squash method. It will likely take somewhere between 45 minutes and 1 1/2 hours. Let cool for at least 15 minutes, then scoop out the seeds and core (if you didn’t before roasting), and serve, peel and mash, or purée.

How to Roast Cubed Butternut Squash

This is the best method to get those bite-sized cubes that make meal prep (hello grain bowls and simple salads!) a breeze. Peel the butternut squash with a vegetable peeler and then trim off the top and tail. Separate the long neck from the bottom (where the seeds and core are) and slice about 1-inch thick, then cube the slices. Cut the bottom in half, then seed and core before slicing into 1-inch thick wedges. Cube the wedges and add all the cubes to a nonstick, parchment paper-, or aluminum foil-lined baking sheet.

Toss the squash with olive oil, salt, and pepper and whatever spices you desire before roasting at 375–400°F for about 30 minutes. The squash should be fork tender, and a bit caramelized on the bottom. Let cool before packing up in an airtight container and storing in the fridge for easy grab-and-go, just-throw-it-together meals. You can can also use this method for roasting any wedges or slices of squash.

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