Maple Roasted Squash Salad

Arugula and roasted acorn squash salad  goat cheese dressing sunflower seeds and pomagranates on a plate
Tap any image to pin it.

Peppery arugula and a zingy, creamy goat cheese dressing elevate this bright, colorful roasted acorn squash salad to heights worthy of your holiday table.

Squash Salad Season is Upon Us. 

Fall—even into late November and early December—is a time of bounty. It’s harvest season, and your local grocery stores and farmers markets should be bursting with a cornucopia of classic autumnal goodies the most iconic of which is, arguably, winter squash. Despite their often-tough skins, winter squash is one of the easiest and most rewarding things to prepare. Here, we’ve taken advantage of the sweet, starchy richness of acorn squash to give this squash salad heartiness and depth, and to provide contrast to the sharp, goat cheese-based dressing. 

The Best Thanksgiving Salad.

Singing with the brightest and cheeriest flavors of the season, this composed maple roasted squash salad makes for a light main dish—just add some crusty bread—or a gorgeous side dish for your family’s holiday meal. It’s also a great one to assemble ahead of time and serve at room temperature (wait to add the dressing until the last minute), or bring to a festive potluck. Star-shaped slices of maple-slicked squash, resting atop a bed of arugula, studded with glinting pomegranate seeds, all dressed in a luscious drizzle of salty, creamy, homemade goat cheese dressing—however you decide to serve this squash salad, we promise rave reviews across the board. 

Arugula and roasted acorn squash salad  goat cheese dressing sunflower seeds and pomagranates on a plate with serving spoon

How Do You Make Squash Salad?

Thick-skinned, lumpy and admittedly a little hard to cut into, winter squash can be weirdly intimidating. But we think this simple maple roasted squash salad will make a convert out of you—it celebrates squash in all of its delicious sweetness, and comes together quickly and easily. Squash salad isn’t squash salad without squash (say that three times fast) so there’s no way around this step. But! We do have a few tips for making this process a little safer and easier.

First, make sure to use a sharp knife. If you don’t have a knife sharpener of your own, add one to your wish list right now! We love this one. Also, a lot of kitchen supply stores host knife-sharpening events, so keep an eye out for one in your area. A sharp knife is a home cook’s BFF. 

Second, lay one clean kitchen towel on top of your cutting board, and one beneath, to give you additional traction while you cut your squash. Game changer, right?!

Cut the acorn squash in half horizontally and scoop out the seeds and strings, leaving the inside clean.  

Slice the acorn squash halves into 3/4-inch rounds—we’re going for a sunburst or star shape here. 

Ingredients for squash salad olive oil, goat cheese, arugula, pomegranates, maple syrup

Pomegranates 101

Jewel-like and super nutritious, ruby-red pomegranate seeds team up with the roasted acorn squash slices to make this squash salad into a work of culinary art. Much like squash, they require just a little bit of prep, but those juicy, tart-sweet seeds are SO worth it. Here’s how to coax them out of their shell: 

  1. Fill a bowl with cool water. 
  2. With a sharp knife, quarter the pomegranate. 
  3. Submerge a quarter of the pomegranate in the water and, using your thumb, gently nudge the seeds out of their skin. 
  4. Repeat this process with each of the quarters. 

Pith may come off along with the seeds, but it will rise to the surface of the water. Skim it off before straining the pomegranate seeds from the water. 

Tips for making Roasted Squash Salad

Our maple roasted acorn squash salad is, at its core, a simple recipe. But it relies on a few key things to make it work: 

  • Use real maple syrup to brush the acorn squash. Sweetly nutty and complex, real maple syrup has almost nothing in common with imitation—it’s worth the splurge. 
  • Our dressing calls for chevré, which is French for “goat” and in the cheese world refers simply to a goat cheese. Use any fresh goat cheese that you love, but don’t make other substitutions.  
  • Buttermilk in this squash salads’ creamy goat cheese dressing lends an extra tang, and we love its sharp contrast to the sweetness of the squash and spicy arugula. If you prefer the dressing a little more mild, go ahead and use regular milk in its place. 

Planning Your Thanksgiving or Christmas menu?

Lighten up your Thanksgiving or Christmas menu by pairing our Rich Prime Rib with Horseradish Cream Sauce with this maple-kissed, roasted squash salad. Or, knock it out of the park at your next dinner party by serving it with cheesy, savory French Onion Soup for a seriously upscale take on a classic soup-and-salad supper. 

Arugula and roasted acorn squash salad  goat cheese dressing sunflower seeds and pomagranates on a plate

Did You Make This Pomegranate Studded Salad?

If you make this maple roasted squash salad, we’d love to hear about it! Be sure to snap a photo, add it to your Instagram feed or stories and tag us @themodernproper and #themodernproper if you do. Also, feel free to leave a comment on the post and tell your friends where you discovered the recipe. 

Maple Roasted Squash Salad

Serves 6

Salad

1 small acorn squash
4 tbsp real maple syrup
1 cup pomegranate seeds
3/4 cup pepitas (pumpkin seeds)
6 oz baby arugula

Creamy Goat Cheese Dressing

4 oz chevre
1/2 cup olive oil
1/4 cup apple cider vinegar, unfiltered
1/2 tsp salt
1/2 tsp freshly ground black pepper
1/3 cup milk (we used buttermilk)

Method

  1. Preheat oven to 400° Using a sharp knife, carefully slice the acorn squash around its middle horizontally. Scoop out seeds and scrape clean. Slice into ¾ inch thick rounds. Place on a parchment paper lined rimmed baking sheet. Do not let any pieces overlap. Using a pastry brush, brush maple syrup over both sides of squash. Bake for 10-15 minutes until the bottom side of squash is nice and golden brown. Flip and bake for another 10-15 minutes. Brush with maple syrup a second time right after removing from oven. Set aside to cool.
  2. While Squash is baking, prepare the dressing. In a blender mix all ingredients until incorporated.
  3. To prepare the salad for serving, Toss ½ the dressing with the arugula. Slowly add more dressing until the greens are coated with dressing but not weighed down by it. Sprinkle ¾ of the pomegranate and pumpkin seeds toss lightly. Lay roasted squash on top of the salad and sprinkle with remaining seeds.