1. Cook orzo according to package directions.
2. While orzo is cooking, heat olive oil in a skillet over medium-low heat. Working in batches, cook the sausages for two to three minutes per side, or until golden. Set sausages aside and cook butternut squash in the same pan, adding more oil as needed. Cook over low heat, stirring often, for 15 to 20 minutes, or until softened. Combine cooked orzo, sausages, butternut squash, and dried cherries in a large bowl.
3. Combine all dressing ingredients in a jar and shake well. Pour over orzo salad and toss to coat.
Tips: Make Ahead: Toss the orzo, squash, and sausages together. Cover and refrigerate. Reheat gently or serve at room temperature. Toss with dressing and dried cherries before serving.