Roasted Hasselback Butternut Squash Salad

Excited to bring you this impressive, yet simple roasted hasselback butternut squash salad! Beautiful squash gets roasted, scored, and roasted again with a syrupy maple glaze. It’s put together with peppery arugula, a tangy caramelized shallot & dijon vinaigrette, maple pecans, and creamy goat cheese. It’s one of the very best combinations of flavors for fall and would make such a stunning side dish for any upcoming holiday dinner!

Roasted Hasselback Butternut Squash Salad

After seeing this hasselback butternut squash technique in Bon Appetit a few years back, I’ve been dying to try it out. It’s simply such a gorgeous presentation that’s festive and mouth watering at the same time.

I ended up making a salad of sorts out of it, with the idea being you can cut pieces off of the roasted squash and eat it along with a sweet and savory arugula salad. I pulled in some of my favorite fall flavors, making this (in my opinion) one of the very best combinations – sage, shallots, maple, dijon, pecans, and goat cheese. It all comes together so beautifully, with lots of texture and contrasting ingredients pairing with the sweet butternut squash.

Roasted Hasselback Butternut Squash Salad

how to roast a hasselback butternut squash

The squash is of course the star in this recipe. Hopefully the step-by-step photos help you visualize how to roast a hasselback butternut squash. It’s actually very simple…with the main varying factor being the size of your squash. I bought one around 2 ¾ lbs, which ended up taking just about 50 minutes total to roast. As the size of the squash increases, so will the cooking time.

Here are the main steps…

  • Peel the squash
  • Cut it in half lengthwise and scoop out the seeds
  • Roast initially with olive oil, salt, and pepper…until tender enough to pierce with a knife
  • Deeply score the exterior of the squash in small increments, without cutting all of the way through
  • Brush with a syrupy glaze
  • Continue to roast until tender and caramelized

If your squash isn’t tender after the time I have listed in the recipe, continue to roast it in 5 minute increments, checking it’s tenderness and caramelization as you go. My best tip when it comes to roasting anything is to use your senses – when it’s ready, you’ll know! You want the squash to be soft, but not mushy. And golden, but not burnt.

Roasted Hasselback Butternut Squash Salad

Once you’ve got the squash going, you’ll get everything else ready to assemble! The caramelized shallots from the glaze turn into a deliciously simple vinaigrette, pecans get toasted in olive oil and simmered with a splash of maple syrup, and creamy goat cheese gets crumbled into bite-sized pieces. Plate it all up on a big platter for the MOST impressive side dish.

Maybe test it out this weekend along with an apple & bacon grilled cheese sandwich for a fun dinner, then save the recipe for your Thanksgiving menus as well! I’d say it’s never too early to plan for the holidays. Enjoy!

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Roasted Hasselback Butternut Squash Salad

Roasted Hasselback Butternut Squash Salad

roasted hasselback butternut squash salad with arugula, caramelized shallot & dijon vinaigrette, maple pecans, and creamy goat cheese

servings: 4-6

Ingredients

Scale
  • 1 (approximately 2 ¾ lbs) butternut squash
  • olive oil
  • kosher salt
  • freshly cracked black pepper
  • 6 leaves fresh sage
  • 1 large shallot, thinly sliced
  • 7 tbsp maple syrup
  • 3 tbsp white wine vinegar
  • 1 tbsp dijon mustard
  • 1 tbsp water
  • ¼ cup vegetable oil
  • 4 oz halved pecans
  • 2 oz arugula 
  • 4 oz creamy goat cheese, crumbled
  • flaky sea salt (optional)

Instructions

  1. Preheat the oven to 425°F. Peel the butternut squash until you reach the pure yellow-orange layer (there should be no white remaining). Cut the squash in half lengthwise. Scoop out the seeds/stringy flesh. Place the squash onto a sheet pan and drizzle generously with olive oil. Rub to coat evenly. Season with salt and freshly cracked black pepper. Roast the squash, halved-side down, for 20 minutes. 
  2. Meanwhile, heat a 2qt saucepan over medium heat. Add about 2 teaspoons of olive oil. Place the sage leaves in the hot oil and fry until crisp, just a minute or so. Transfer the sage to a plate. Add the sliced shallot to the oil. Saute for a few minutes until caramelized. Season with a pinch of salt. 
  3. Stir in 3 tablespoons of maple syrup, 2 tablespoons of white wine vinegar, the dijon, and water. Bring the mixture to a simmer. Lower the heat and cook for about 5 minutes until syrupy. Transfer the shallots to a mixing bowl. Reserve the maple glaze. 
  4. Remove the squash from the oven. Use a sharp knife to score the outside of the squash in small increments (see photos above). Cut each slice about ¾” of the way into the squash, without cutting all the way through. Brush the maple glaze over the squash. Continue to roast for about 30 more minutes, or until tender. 
  5. Add 1 tablespoon of maple syrup and the remaining 1 tablespoon of white wine vinegar to the shallots. Whisk to combine. Slowly whisk in the vegetable oil. Season with a pinch of salt to taste. 
  6. Heat a skillet over medium heat. Add enough olive oil to coat the bottom. Add the pecans. Toast for a couple of minutes until golden and fragrant. Stir in the remaining 3 tablespoons of maple syrup and a pinch of salt. Simmer for about 3 minutes until reduced. 
  7. Toss the arugula with half of the shallot vinaigrette and arrange it onto a platter. Use a metal spatula to carefully transfer the butternut squash from the sheet pan to the platter. Top with the maple pecans, goat cheese, and fried sage. Drizzle the remaining vinaigrette over the squash. Sprinkle with flaky sea salt.

Notes

The larger your butternut squash is, the longer you’ll have to roast it. Adjust times as needed.

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