These Roasted Brussels Sprouts and Butternut Squash are topped with pan-fried halloumi, dates, olives, parsley, and orange tahini dressing. This side dish pairs well with chicken, fish, and beef. The perfect colourful fall side dish!

Oddly enough, I’ve always enjoyed Brussels sprouts, no matter how they are cooked. But my favourite way to enjoy them, by far, is roasted! Roasting Brussels sprouts with a bit of oil, salt, herbs, and pepper until they are lightly browned and crispy makes them hard to pass up… and dare I say, addictive!
I started with the idea of roasted Brussels sprouts and butternut squash and came up with this delicious fall side dish. I think of it as a warm roasted veggie salad. While the veggies are roasting, you’ll pan fry some halloumi cheese. Halloumi is a firm cheese of Middle Eastern origin that has a high melting point. It does not melt during frying, but browns up beautifully. I’ve used it in a number of recipes, including this hummus with halloumi and these turkey burgers. Then, you’ll add some dates, olives, and an orange tahini dressing.
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ingredients you’ll need
For the roasted Brussels sprouts and squash, you’ll need Brussels sprouts, squash or sweet potato, extra-virgin olive oil, thyme, hot red pepper, flakes, garlic, sea salt, and pepper.
For the orange tahini dressing, you’ll need extra-virgin olive oil, tahini, orange juice and zest, garlic, sea salt, pepper, lemon juice and zest, whole grain mustard, and honey.
For the toppings, you’ll need halloumi cheese, Medjool dates, olives, and parsley.

INSTRUCTIONS
Roast the Brussels sprouts and squash: Preheat the oven to 425 F and line two large, rimmed baking sheets with parchment paper. Place the Brussels sprouts in the centre of one baking sheet and the squash on the other. Sprinkle the Brussels sprouts with half of the thyme, half of the hot red pepper flakes, sliced garlic, and a pinch of salt and pepper. Drizzle with 1 ½ tablespoons of oil and toss to coat. Spread out in an even layer.

Place the squash in the centre of the second baking sheet. Sprinkle with half of the thyme, half of the hot red pepper flakes, and a pinch of salt and pepper and drizzle with the remaining 1 ½ tablespoons of oil. Toss to coat and spread out in an even layer.

Roast the squash for 25 minutes and the Brussels sprouts for 15-20 minutes. Halfway through the Brussels sprouts roasting, stir and return to the oven.
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While the squash and Brussels sprouts are roasting, fry the halloumi: Warm a large cast iron skillet over medium-high heat. Once hot, add the halloumi in a single layer and cook until browned on both sides, about 3 minutes per side. Initially, a lot of liquid will come out of the cheese and will steam and foam quite a bit, but it evaporates and then the cheese browns. If it is browning too quickly, turn down heat to medium. Remove from the heat and set aside.

Make the orange tahini dressing: In a bowl, whisk together the oil, tahini, zest and juice of the orange and lemon, garlic, salt, pepper, mustard, and honey.

Assemble: Arrange the Brussels sprouts and squash on a platter. Top with the halloumi, dates, olives, and parsley. Drizzle with the dressing. Enjoy!

Substitutions and Variations
- Halloumi: Use ½ cup of crumbled feta cheese instead.
- Butternut Squash: Use the same amount of peeled and cubed sweet potato. Roast for the same amount of time.
- Brussels Sprouts: If you do not like Brussels sprouts, use broccoli. Roasting time is the same.
- Dates: You can use¼ cup dried cranberries instead of the dates.
FALL SALAD RECIPES
If you enjoy these roasted Brussels sprouts and butternut squash, you’ll also enjoy these fall salad recipes:
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Roasted Brussels Sprout + Butternut Squash
- Total Time: 40 minutes
- Yield: 6 servings 1x
Description
Roasted Brussels Sprouts with Butternut Squash, pan-fried halloumi, dates, olives, parsley, and orange tahini dressing is the perfect side dish.
Ingredients
Brussels Sprouts and Squash
- 4 cups Brussels sprouts, halved lengthwise
- 4 cups peeled, cubed butternut squash or sweet potato (1 inch cubes)
- 4 garlic cloves, sliced
- 2 teaspoons dried thyme
- ½ teaspoon hot red pepper flakes
- Couple pinches each sea salt and freshly ground black pepper
- 3 tablespoons extra-virgin olive oil
Halloumi
- 4–8 ounces halloumi cheese, sliced (depending on how much cheese you want in your salad)
Orange Tahini Dressing
- 2 tablespoons extra-virgin olive oil
- 2 tablespoons tahini
- Zest of 1 orange
- ¼ cup freshly squeezed orange juice
- Zest of 1 lemon
- 2 tablespoons freshly squeezed lemon juice
- 1 large garlic clove, minced
- ¼ teaspoon sea salt
- Freshly ground black pepper, to taste
- 1 tablespoon whole grain mustard
- 1 tablespoon honey
Toppings
- 4 pitted Medjool dates, chopped
- Big handful of fresh parsley, chopped
- ⅓ cup green or Kalamata olives
Instructions
- Roast the Brussels sprouts and squash: Preheat the oven to 425 F and line two large, rimmed baking sheets with parchment paper. Place the Brussels sprouts in the centre of one baking sheet and the squash on the other. Sprinkle the Brussels sprouts with half of the thyme, half of the hot red pepper flakes, sliced garlic, and a pinch of salt and pepper. Drizzle with 1 ½ tablespoons of oil and toss to coat. Spread out in an even layer.
- Place the squash in the centre of the second baking sheet. Sprinkle with a pinch of salt and pepper and drizzle with the remaining 1 ½ tablespoons of oil. Toss to coat and spread out in an even layer.
- Roast the squash for 25 minutes and the Brussels sprouts for 15-20 minutes. Halfway through the Brussels sprouts roasting, stir and return to the oven.
- While the squash and Brussels sprouts are roasting, fry the halloumi: Warm a large cast iron skillet over medium-high heat. Once hot, add the halloumi in a single layer and cook until browned on both sides, about 3 minutes per side. Initially, a lot of liquid will come out of the cheese and will steam and foam quite a bit, but it evaporates and then the cheese browns. If it is browning too quickly, turn down heat to medium. Remove from the heat and set aside.
- Make the orange tahini dressing: In a bowl, whisk together the oil, tahini, zest and juice of the orange and lemon, garlic, salt, pepper, mustard, and honey.
- Assemble the salad: Arrange the Brussels sprouts and squash on a platter. Top with the halloumi, dates, olives, and parsley. Drizzle with the dressing. Enjoy!
- Prep Time: 15 minutes
- Cook Time: 25 minutes
- Category: Salad, Side Dish
Nutrition
- Serving Size:
- Calories: 386
- Sugar: 18.2 g
- Sodium: 480.8 mg
- Fat: 21.7 g
- Saturated Fat: 6.3 g
- Carbohydrates: 43.8 g
- Fiber: 7 g
- Protein: 10.9 g




Natalie says
So creative. I love your recipes and this is an amazing vegetable dish.
Allison says
Aw, thank you so much! It means a lot to hear that and I’m really happy you enjoyed this!
Jeremy says
This is so very good. What a terrific idea to add halloumi, and the dressing is superb too!