Sweet, tender, and perfectly caramelized, this roasted acorn squash with kale pesto, dried cherries, and toasted walnuts is a perfectly cozy fall-flavored side dish.


Fall squash recipes are versatile and warm, with dishes like my butternut squash and shittake mushroom lasagna and my beef stew with butternut squash screaming “comfort food!”. Recently I thought it would be fun to take my traditional basil pesto recipe and give it a fall makeover, so I came up with a kale pesto version made with toasted walnuts and sage. Pairing these warm and earthy flavors together felt right, and that’s how this roasted acorn squash with kale pesto was born.

In this recipe, I roast nutty acorn squash rings (skin-on) then dollop the caramelized squash with pesto, and add some plumped-up dried tart cherries with toasted walnuts for extra flavor and crunch. This easy-to-make side is earthy, nutty, and delicious, and would be an excellent addition to your Thanksgiving spread this year.


What’s In This Roasted Acorn Squash

Here’s what you need for this easy acorn squash side dish:

  • Acorn squash
  • Extra-virgin olive oil
  • Kosher salt and freshly ground black pepper
  • Toasted walnuts
  • Tart dried cherries
  • Kale pesto

How to Make Roasted Acorn Squash

This roasted acorn squash dish is extra simple, especially when you’ve made the kale pesto ahead of time. But if you haven’t, the pesto is easy to whip up while the squash is roasting.

Here’s how to make this side dish:

Grab your sharpest, heavy knife and slice. Cut the squash in half, lengthwise, stem to stem. Use a sturdy spoon to scrape and scoop out the insides and discard them. Slice each squash halve into 1-inch-thick half moon rings.

Roast the squash until caramelized. Drizzle the rings with olive oil then season with kosher salt and black pepper. Roast at 400°F for about 30 minutes or until soft and nicely caramelized.


Make the Kale Pesto

Like any pesto, this kale version is versatile. You could omit the sage if you like, or experiment with toasted almonds or even pepitas instead of walnuts. You can make the pesto up to 1 week ahead of time or on the fly while your squash roasts.

Toast your nuts. This gives them more flavor. You can do this on the stovetop or in the oven.

I keep things simple and make this pesto recipe in the food processor. Add the toasted walnuts, Parmesan cheese, and garlic to the bowl of the food processor and process until finely minced. Add the kale and sage and process. Slowly stream in the olive oil through the chute. Season with fresh lemon juice, kosher salt, and freshly ground black pepper. Taste and adjust if necessary.

Plump up the dried cherries. Combine the cherries, water, and vinegar in a small saucepan, over low heat then simmer for 2-3 minutes, or until the cherries are plump.

Put it all together. To serve, measure about ¼ cup of the pesto and dollop over the squash (use more or less if you like). Then top with toasted walnuts and cherries and serve immediately.


Do You Eat the Skin of Acorn Squash?

It depends on the recipe, but roasting acorn squash makes its skin tender and edible. In this dish, the squash slices are on the thinner side, so you won’t get a huge chunk of skin. I prefer leaving the skin on for the color and texture it adds, but you can easily remove it (I find it’s easier to do this after roasting rather than peeling the whole squash beforehand).

How to Cut an Acorn Squash for Roasting

  • Sharpen that knife, chef. First thing first, make sure you’ve got a heavy, sharp knife. Stand the squash up and slice it in half down the middle, from stem to stem.
  • Scoop out the seeds and innards. Use a sturdy spoon for this (a grapefruit spoon works great if you have one).
  • Slice into half-moon rings. Lay each squash halve on the cutting board and cut crosswise, into 1-inch-thick slices.

What to Serve With This Roasted Acorn Squash

More Fall Squash Recipes to Try

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