steak salad with chilis and squash

Harvest Steak Salad with Chili Roasted Squash

Last Updated on August 21, 2023

Autumn and winter salads are so often topped with super-sweet ingredients like dried cranberries and candied nuts—but you can enjoy the flavors of the seasons without the over-the-top sweetness. Add spices like chili powder and rosemary, a touch of sweetness with balsamic vinegar, butternut squash, and a strategic touch of maple syrup (plus a bit of funkiness from blue cheese), giving this salad the layers of deep flavor you want as the air starts to feel chilly outside.

Miso (fermented soy paste) in the dressing serves a couple of purposes: It emulsifies the dressing and adds a distinctive taste that stands up to the other flavors in the salad. 

A rich, beefy steak like flat iron is the perfect centerpiece for this healthy meal. It’s hearty and full of flavor, it’s easy to cook and it’s always a crowd-pleaser. 


steak salad with chili roasted squash

Harvest Steak Salad with Chili Roasted Squash

5 from 2 votes
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Protein: Beef
Course: Lunch, Main Course
Prep Time: 25 minutes
Cook Time: 50 minutes
Servings: 4
Author: Beth Lipton


  • 3 tablespoons balsamic vinegar divided
  • 6 tablespoons extra virgin olive oil divided
  • 2 cloves garlic minced or grated on a microplane
  • 1 ½ teaspoons minced fresh rosemary leaves or ½ teaspoon dried
  • Fine sea salt
  • Freshly ground black pepper
  • 1 ½ pounds flat iron steak pat dry
  • 1 1 ½- to 2- pound butternut squash peeled, seeded, cut into ½-inch cubes (about 4 cups)
  • 1 teaspoon chili powder
  • ½ teaspoon garlic powder
  • 1 tablespoon Dijon mustard
  • 2 teaspoons white miso
  • ¼ teaspoon maple syrup
  • 1 tablespoon avocado oil
  • 1 romaine heart chopped (about 5 cups)
  • ½ English cucumber quartered lengthwise, chopped (about 1 cup)
  • 6 medium radishes halved, sliced (about ½ cup)
  • ¼ cup roasted salted pepitas
  • ¼ cup crumbled blue cheese


  • In a small bowl, whisk together 2 tablespoons vinegar, 2 tablespoons olive oil, garlic, rosemary, ½ teaspoon salt, and ¼ teaspoon pepper. Place the steak in a bowl or container; pour in the marinade and turn to coat. Cover and refrigerate for at least 1 hour or up to 6 hours. Remove the steak from the fridge 1 hour before cooking.
  • Preheat the oven to 425ºF. Line a large baking sheet with parchment paper. In a large bowl, combine the cubed squash, 1 tablespoon olive oil, chili powder, garlic powder, ½ teaspoon salt, and ¼ teaspoon pepper; toss to coat. Spread in a single layer on the baking sheet and roast until tender and caramelized in spots, 35 to 40 minutes, stirring once or twice during roasting time.
  • Make the dressing: In a small bowl, whisk together remaining 1 tablespoon balsamic vinegar, mustard, miso, maple syrup, 3 tablespoons olive oil, and ¼ teaspoon pepper until well blended. Whisk in hot water 1 teaspoon at a time to thin to desired consistency. Taste and season with salt and additional pepper, if needed. (Yield: About 1/3 cup. You can make the dressing up to 2 days ahead. Cover and keep at room temperature. Whisk well before using.)
  • Preheat a large cast-iron skillet over medium-high heat until very hot. Remove the steak from the marinade (discard marinade). Pat the steak dry thoroughly; season generously with salt. Swirl the avocado oil in the skillet, then add the steak. Cook undisturbed until seared on one side, 3 to 4 minutes. Carefully flip and cook until medium-rare (an instant-read thermometer stuck into the thickest part should read between 125ºF-130ºF), 3 to 4 minutes longer. Transfer to a cutting board, tent with foil, and let rest for 5 to 10 minutes.
  • In a large bowl, combine the romaine, cucumber, and radishes. Add 3 tablespoons dressing and a few pinches of salt and pepper; toss to combine. (Toss in more dressing, if desired.) Add the squash; carefully toss. Divide among 4 plates or shallow bowls. Slice the steak against the grain and divide among the salads. Top with pepitas and blue cheese; serve immediately.
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Beth Lipton is a Brooklyn-based recipe developer and writer specializing in food and wellness. Her work has appeared in Clean Eating, Paleo magazine,, Well+Good, Outside, and more. Beth's latest cookbook, Carnivore-ish, featuring 125 animal protein-forward recipes, is available now.