Line a baking sheet with foil or parchment. Toss the vegetables and the bacon with salt + pepper in the olive oil in a large bowl and pour it onto the baking sheet.
Place in the oven for 25-30 minutes until the brussels are crispy and there is some caramelization on the squash. Pour the vegetables into a large bowl.
Add the dried cranberries to the bowl of vegetables.
For the toasted pecans
Place pecans in the 425 degree oven on a baking sheet for 5 minutes to toast them. Remove, then add to the rest of the vegetables
For the dressing
Whisk together the dressing components. Pour onto the vegetables and place into a serving dish or salad bowl. Serve warm or room temperature.