Preheat the oven to 400 degrees F (200 degrees C). Line a rimmed baking sheet with foil or parchment; place bacon on the sheet.

Bake bacon in the preheated oven until crisp, about 10 minutes. Remove bacon from tray and drain on paper towels. Reserve drippings in the pan.

Increase the oven temperature to 425 degrees F (220 degrees C).

Add butternut squash, onion, 2 tablespoons olive oil, 1 teaspoon salt, ½ teaspoon pepper, and thyme to the pan with bacon drippings and toss to coat.

Roast squash in the preheated oven until browned, about 20 minutes. Set aside.

Meanwhile, bring a large pot of lightly salted water to a boil. Cook orzo in the boiling water, stirring occasionally, until tender yet firm to the bite, about 10 minutes. Drain and set aside to cool.

For vinaigrette, add vinegar, maple syrup, mustard, garlic powder, remaining salt, and pepper into a bowl. Whisk in olive oil until well combined. Set aside.

Add pasta, Brussels sprouts, walnuts, cranberries, and vinaigrette to a large bowl and toss to combine.