Think salad is just a summer thing? Let me show you how this roasted acorn squash pear and kale salad with gorgonzola crumbles, cranberries, and candied pecans will change your mind forever!

Roasted Acorn Squash Pear and Kale Salad

When I want a salad, I want a SALAD. A meal. Something that’s going to fill me up and satisfy me for hours. Or, at least until snack time rolls around.

There are a few salads that meet this requirements that I keep coming back to and that I keep in my close meal rotation. In the summer, it’s grilled sweet corn and zucchini panzanella with a fresh herb vinaigrette along with my very favorite, incredibly easy, and showstoppy cobb salad for two with a genius homemade caesar dressing.

Roasted Acorn Squash Pear and Kale Salad

In the winter, it’s this chopped roasted winter veg salad with chicken and that carrot and sesame-spiced baked turkey meatballs with tahini dressing that really do it for me. Both are so warm and comforting!

And in the fall, my go-tos over the past few years have, hands down, been some of the best meals I’ve ever made. My sweet and salty fall harvest and warm kale and quinoa with maple dijon grilled chicken salads both continue to knock our salad socks off (umm…if there was such a thing?). I’m certain this has to do with one common factor:

Roasted Acorn Squash Pear and Kale Salad

The maple dijon vinaigrette.

Oh my word YES. That vinaigrette hits on sweet, salty, and tangy/acidy taste sensations and the flavor combination works so perfectly with the ever increasing number of salads I pour it over. It’s practically drinkable.

Roasted Acorn Squash Pear and Kale Salad

This roasted acorn squash pear and kale salad is the latest of my fall salad creations. With acorn squash everywhere now, I felt like I needed to figure out how to do more with it than just scoop-stuff-bake.

So I sliced and roasted it, and then dumped it over some super tender baby kale – which passed for spinach with 2 of the people I served this meal to – and added sliced pears, gorgonzola crumbles, dried cranberries, and sadly not pictured here because I’m a scatterbrain: candied pecans.

Roasted Acorn Squash Pear and Kale Salad

And oh boy did this salad ever deliver, both in big flavor and in the ability to satisfy me as a full meal. With Thanksgiving around the corner (whaaattt??), I definitely foresee more opportunities to push this salad on my house guests show off this gorgeous roasted acorn squash pear and kale salad.

Roasted Acorn Squash Pear and Kale Salad

  • Prep Time: 25min
  • Cook Time: 25-30min
  • Yield: 4 lunch/dinner servings | 6-8 side salad servings

Notes

A few things to note with this recipe: First, I forgot to add the pecans to the salad before I photographed it. Oops! They were a big part of the salad – and a big hit! – when I served it to guests but feel free to skip them or add sliced almonds or chopped walnuts instead.

Also, to make this a vegan meal, simply drop the gorgonzola crumbles.

Instead of serving on individual plates, there’s absolutely nothing wrong with throwing all of the salad parts into a salad bowl, drizzling with the vinaigrette, and serving it family style. This is how I served the salad the first time I made it and no one blinked an eye about the presentation.

And lastly, don’t try peeling the squash like you would peel a butternut squash – it just won’t work. You can eat the skins after the squash has been roasted. However, they might be a little tough for some people. I had no issues and loved the added flavor (and extra fiber) but feel free to cut the squash out of the skins either before you roast (after you slice them into half-moons) or after.

Ingredients

2 medium acorn squash, sliced in half horizontally with seeds and stringy flesh scooped out (see note above)
Extra virgin olive oil
Kosher salt and ground black pepper
1 cup halved pecans
2 tbsp unsalted butter
3 tbsp brown sugar
12 cups baby kale
2 pears, cored and thinly sliced lengthwise
Gorgonzola crumbles
Dried cranberries
Maple dijon vinaigrette

Instructions

  • 01

    To make the acorn squash: Preheat oven to 425° F. Ready 2 large baking sheets.

    Arrange the squash halves skin side-down in a 13×9-inch glass or microwave-safe dish. Drizzle about a ¼-inch of water into the bottom of the dish. Cover with plastic wrap and microwave on high for 5 minutes. Remove the plastic wrap, dry off the wet bottoms of the squash, and transfer to a large cutting board. This par-cooking step will make it easier to slice the squash and speed up the roasting time.

    With the squash set on its skin sides (so: tops or bottoms facing the board – not the rounded sides), slice the halves into quarters, this time vertically through the centers. Cut each quarter into half-moon slices about ½-inch thick or just a little less – it doesn’t have to be exact.

    Transfer the half-moons to the baking sheets and drizzle with some olive oil then sprinkle a good pinch of kosher salt and black pepper over the squash. Flip the half-moons over to coat them with oil, salt, and pepper.

    Roast for 25 to 30 minutes, flipping the squash over halfway through the time.

  • 02

    While the squash roasts, make the candied pecans. Ready a Silpat or line a baking sheet with parchment paper; set aside.

    Heat the butter and brown sugar over medium heat in a medium nonstick pan until bubbling. Toss the pecans into the butter-sugar mixture until coated. Cook, stirring occasionally, until the sugar liquefies and turns a dark amber color.

    Pour the pecans out onto the Silpat or parchment paper and spread them out with a rubber spatula. Allow them to cool completely before breaking them up into clusters.

  • 03

    Assemble the salad: Divide the kale between 4 dinner plates and top each with a few pieces of squash, half of one of the pears, then sprinkle the gorgonzola crumbles, dried cranberries, and candied pecans over the salad. Finish with a drizzle of the maple dijon vinaigrette. Serve while squash is still warm.

  • 04

    Do ahead: The roasted squash will keep for up to 2 days in an airtight container in the fridge if you want to get a head-start on preparation. Just heat it up in a 350° F oven or the microwave for a few minutes before adding to the salad. As well, the candied pecans and vinaigrette can be made and stored in the fridge for up to 2 weeks before you make the salad.

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