Warm Butternut Squash & Brussel Sprout Salad Recipe

Prepare oven and vegetables

Preheat oven to 425°F (220°C). Peel and seed the butternut squash, then cut into 1/2-inch cubes. Trim the stem ends of Brussels sprouts, halve large ones so all are roughly bite-sized.

Toss squash and Brussels sprouts with 2 tablespoons olive oil, 1 teaspoon kosher salt, and 1/2 teaspoon black pepper in a large bowl until evenly coated. Spread in a single layer on a rimmed baking sheet, leaving space so they roast rather than steam.

Roast in the preheated oven for 22–28 minutes, stirring or turning once halfway through, until squash is tender and caramelized at edges and sprouts are browned and crisp-tender. Remove from oven and let cool slightly.

While vegetables roast, cook the bacon. Preheat a large skillet over medium heat. Add bacon slices in a single layer and cook, turning occasionally, until crisp, about 7–9 minutes. If using maple syrup, brush a little on each slice in the last 1 minute of cooking and allow it to glaze.

Transfer cooked bacon to a paper towel–lined plate to drain and cool, then chop into 1/2-inch pieces.

Roast garlic

Lower oven to 400°F (204°C) after vegetables finish or roast garlic at the same time in a separate small foil pouch. Place 4 unpeeled garlic cloves on a small piece of foil, drizzle with 1 teaspoon olive oil, wrap into a pouch and roast for 18–20 minutes until soft and caramelized. Alternatively, microwave 40–60 seconds until soft if short on time.

Squeeze the softened garlic flesh from skins into a small bowl and mash with a fork. Whisk together mashed roasted garlic, 1/2 cup mayonnaise, 1/2 cup sour cream, 1/4 cup buttermilk (add more to thin as desired), 2 tablespoons chopped parsley, 1 tablespoon chopped chives, 1/2 teaspoon dried dill, 1 teaspoon lemon juice, 1/2 teaspoon kosher salt and 1/4 teaspoon black pepper until smooth. Taste and adjust seasoning or acidity.

Line a baking sheet with parchment paper or a silicone mat. Preheat oven to 400°F (204°C) if not still hot. Place tablespoon-sized mounds of finely grated sharp cheddar (about 1 tablespoon each) spaced 1–2 inches apart. Flatten slightly into thin rounds and sprinkle a tiny pinch of paprika on each, if using.

Bake 5–8 minutes until edges are bubbling and just turning golden. Remove and let crisps cool on the pan for 5 minutes — they will crisp further as they cool. Transfer to a wire rack to cool completely.

In a large mixing bowl combine warm roasted butternut squash and Brussels sprouts with baby arugula or mixed greens. Add chopped bacon, 1/2 cup dried cranberries and 1/2 cup toasted chopped pecans or walnuts.

Drizzle 1/2 to 3/4 cup of the roasted garlic ranch dressing over the salad (reserve extra dressing for serving). Toss gently to combine — the warmth of the vegetables will slightly wilt the greens and meld flavors. Taste and adjust with additional salt, pepper or lemon juice if needed.

Divide salad onto 4 plates or bowls (servings). Garnish each portion with 2–3 cheddar crisps broken into pieces and any remaining chopped herbs or extra dried cranberries.