Preheat your oven to 400°F. Toss butternut squash cubes with 1 tbsp olive oil, salt, and pepper on a baking sheet. Roast for 20-22 minutes until golden and fork-tender, stirring halfway through. The edges should caramelize slightly for maximum sweetness and depth of flavor.
On a separate baking sheet, toss Brussels sprouts halves with remaining olive oil, salt, and pepper. Place both sheets in the oven together, ensuring they roast simultaneously for convenience and timing efficiency. Roast for the same 20-22 minutes, shaking the Brussels sprouts pan halfway through until they're crispy outside and tender inside.
While vegetables roast, whisk together apple cider vinegar, maple syrup, and Dijon mustard in a small bowl. Taste and adjust seasonings—this is your chance to balance sweet, tangy, and sharp flavors perfectly. Set the vinaigrette aside at room temperature; it will emulsify slightly as it sits and mingles.
Slice your Granny Smith apple just before assembly to prevent browning. You want bright, crisp apple pieces that provide textural contrast and fresh acidity throughout the cozy fall salad side recipe experience. The tartness of Granny Smith apples complements the sweetness of roasted vegetables beautifully.
Place mixed fall greens in a large bowl and drizzle lightly with half the vinaigrette. Toss gently to coat evenly without overdressing, which would wilt the delicate leaves too quickly. Transfer to serving plates or a large platter for family-style dining.
Top each portion with roasted butternut squash, Brussels sprouts, dried cranberries, candied pecans, and pumpkin seeds in an aesthetically pleasing arrangement. Scatter apple slices and crumbled goat cheese over everything, then drizzle with remaining vinaigrette just before serving for optimal freshness.