Preheat oven to 400 degrees. Toss the cubed squash with the olive oil and season with salt and pepper. Spread onto a baking sheet and roast for 30 minutes.
While the squash is roasting, toast the pine nuts: Heat the pine nuts in a small, dry frying pan over medium heat. Continue to move them around the pan until they start to brown and become fragrant. Remove onto a paper towel.
To make the dressing, place all ingredients in a glass jar or plastic container with a lid. Seal tightly and shake vigorously until all ingredients are combined.
Assemble the salad ingredients in a large bowl, place roasted squash on top and dress generously.