Slice squash horizontally in half and then vertically down the center, scoop out the seeds and save them. Peel the squash.
Cut squash, apples and onions into 2-inch cubes. Place in a large bowl, add whole garlic cloves and drizzle with olive oil, toss to coat.
Put the squash apples and onions on a baking sheet lined with parchment paper. Sprinkle with kosher salt and bake in the oven for about 35 minutes (or until almost tender).
While the squash is roasting, clean any stringy bits from the seeds, place them on a sheet pan lined with parchment paper and sprayed with olive oil. Lightly spray the tops of the seeds with oil and dust with seasonings of your choice. I like to use a little curry powder, kosher salt and granulated garlic. Place them in the oven to roast until golden brown, approx. 15 min.
Next, in a large stock pot, add stock, herbs, and squash mixture and bring to a boil. Cover, reduce heat, and simmer for about 15 minutes (or until the squash is very tender).
Puree stock with a handheld stick blender, or puree in batches in a regular blender or food processor, adding milk slowly until the soup reaches the desired consistency.
Season with salt and pepper to taste and garnish with toasted seeds.
• If you don't want to deal with cutting up a whole squash, purchase peeled, diced squash from the produce section.
• This soup can be frozen