Bake the bacon. Heat the oven to 400°F. Arrange the bacon on a rimmed sheet pan. Bake 12–15 minutes until crisp. Transfer the bacon to paper towels, reserving 1 tbsp of the drippings in the pan.

Raise the heat and roast the squash. Increase the oven to 425°F. Toss the butternut squash and red onion with the olive oil, bacon drippings, ½ tsp salt, ¼ tsp pepper, and thyme directly in the pan. Roast 15 minutes.

Add the Brussels sprouts. Pull the pan out, push the squash to one side, and add the Brussels sprouts cut-side down. Season with the remaining salt and pepper. Roast 12–14 minutes more, until the squash is tender and the Brussels are charred at the edges.

Cook the orzo. Bring a large pot of well-salted water to a boil. Cook the orzo 8–9 minutes, until al dente. Drain and do not rinse.

Dress the pasta warm. Immediately toss the drained orzo with 1 tbsp olive oil and 3 tbsp of the vinaigrette in a large bowl. The warm pasta will absorb the dressing. Spread it on a sheet pan to cool for 10 minutes.

Make the vinaigrette. Whisk the cider vinegar, maple syrup, whole grain mustard, Dijon, garlic powder, salt, and pepper in a jar. Slowly stream in the olive oil while whisking until emulsified.

Toast the walnuts. In a dry skillet over medium heat, toast the walnuts 4–5 minutes, stirring often, until fragrant and lightly browned. Remove immediately.

Assemble. Add the cooled orzo to a large bowl with the roasted vegetables, chicken, chickpeas, and the remaining vinaigrette. Toss gently.

Finish with the crisp elements. Fold in the bacon, walnuts, cranberries, feta, and parsley. Add the lemon juice. Taste and adjust salt.

Serve or chill. Serve at room temperature, or refrigerate in containers for up to 4 days. Add a splash of vinaigrette or lemon before serving if the pasta has absorbed the dressing.