4 Pounds (about 2 medium or 1 large) whole butternut squash
1 Tablespoon Canola Oil
2 Tablespoons Unsalted Butter
2 Cups Large Diced Onion (about 1 medium onion)
2 Cups Diced (about 1 medium) Granny Smith Apple, peeled if desired
1 Clove of Garlic, minced
¼ Teaspoon Crushed Red Pepper Flakes
4 Cups Vegetable or Chicken Broth
1 ½ Teaspoons Kosher Salt, plus more to taste
¼ Teaspoons Freshly Ground Black Pepper, plus more to taste
½ Cup Heavy Cream
8 Fresh Chopped Sage Leaves (1 packed tablespoon)
1. Preheat oven to 375º F and place a rack in the middle. Line a baking sheet with foil.
2. Coat the whole butternut squash in canola oil and place on the lined baking sheet. Roast in the oven for 1 to 1 ½ hours, turning the squash every 20 minutes or until the squash is fork tender.
3. In a large, heavy bottom pot or dutch oven over medium heat, melt the butter. Add the chopped onions and cook until the onions are translucent and just beginning to caramelize.
4. Add the diced apple and cook for 5 minutes or until softened.
5. Add the minced garlic and the crushed red pepper flakes and cook for 1 minute, until fragrant. Remove the pan from the heat and set aside.
6. When the squash is ready remove it from the baking sheet and cool on a rack until able to handle it. Cut the cooled squash in half and use a spoon to scoop the seeds out. Peel off and discard the skin and add the flesh into the pot with the onion mixture.
7. Add the vegetable or chicken broth with the squash and season with the kosher salt. Stir to combine.
8. Bring to a boil over medium-high heat, then reduce the heat to medium-low and simmer for 15 minutes, stirring occasionally to break up any large pieces of squash, until the flavors meld.
9. Remove the pot from the heat, and stir in the cream and the chopped sage.
10. Using a blender, immersion blender or food processor, and in batches if needed, puree the soup until smooth.
11. Taste and season with more salt and black pepper. If desired garnish with the toasted pumpkin seeds.