Cut each butternut squash into 8 even wedges and use a spoon to scoop out the seeds. Then place the squash on a cookie sheet and drizzle with 1 tbsp of the olive oil, 1 tbsp of maple syrup, and 1/4 tsp of salt. Roast for 40 minutes.
Next, chop the onions and apples into 2 inch chunks and place them on the second cookie sheet along with and two whole garlic cloves.
Drizzle with 1 tbsp of the olive oil and sprinkle with 1/4 tsp of salt and 3/4 tsp black pepper. Roast for 30-35 minutes and then remove both trays from the oven and allow the veggies to cool slightly.