Start by preheating your oven to 400 degrees. Cut the acorn squash in half vertically. Clean the seeds out of the squash and rub 1 Tbsp of butter on each half. Sprinkle 1 Tbsp brown sugar on each half, as well as some salt and pepper to taste. Place on a prepared baking sheet (lined with parchment paper) and put in the oven for 45 minutes.
Cut the butternut squash in half horizontally where the neck meets the base. Stand the neck up and peel the skin off the squash with a sharp knife or peeler. Now peel the base, then half and deseed the base. Now cut the squash into 1-inch cubes.
Coat the 1-inch cubes of squash with olive oil, salt, pepper, garlic powder, and fresh rosemary. Add the coated squash to the same pan as the acorn squash when there are about 30 minutes left. Toss butternut squash 2-3 times while cooking.
Once all squash is in the oven, wash and trim your asparagus and place them on a baking sheet lined with parchment paper. Cover with olive oil, salt, and pepper. If you have a grill available, have it preheated to 375 degrees, and add the asparagus, turning a few times, and cook for 15 minutes. (If you do not have a grill available, you can simply add it to the oven)
All items should be finished around the same time and can be kept in the oven at a low temperature to stay warm.
