Ingredient

• 6 tablespoons plus 1 teaspoon olive oil, divided
• 3 medium (about 1 pound 6 ounces each) acorn squash, halved and seeded
• 1/2 teaspoon ground black pepper
• 1 teaspoon fine salt, divided
• 1 large (7 ounces) Honeycrisp apple, roughly chopped (about 2 cups)
• 2 large shallots (about 2 ounces each)  
• 3 garlic cloves, chopped
• 1 (1 1/2-inch) piece fresh ginger, peeled and chopped 
• 4 cups low-sodium vegetable broth
• 1 tablespoon apple cider vinegar
• 1 1/2 teaspoons pure maple syrup

Cheesy Croutons (Optional)

• 1 cup cubed sourdough bread
• 2 tablespoons pre-grated parmesan cheese
• 2 tablespoons olive oil
• 1/4 teaspoon ground black pepper
• 1/4 teaspoon fine salt

Direction

1. Gather the ingredients. Preheat the oven to 425 F with racks in the center and lower third positions. Line 1 large rimmed and 1 small rimmed baking sheet with parchment paper.
2. Brush 2 tablespoons olive oil over 3 medium (about 1 pound 6 ounces each) acorn squash, halved and seeded and sprinkle evenly with 1/2 teaspoon ground black pepper and 1/2 teaspoon fine salt. Place, cut-side down, on the large rimmed baking sheet. Bake on the center rack until tender, about 40 minutes.
3. Meanwhile, toss 1 large (7-ounce) Honeycrisp apple, roughly chopped (about 2 cups) with 1 teaspoon olive oil and spread into an even layer on the small baking sheet. Bake until caramelized on the bottom and very tender, 25 to 30 minutes.   
4. While the squash and apple are baking, roughly chop 1 large shallot and transfer to a small bowl. Thinly slice the remaining 1 large shallot crosswise into thin rings (about 1/16-inch thick). Set aside.
5. Heat the remaining 1/4 cup olive oil in a large Dutch oven over medium-low. Add the thinly sliced shallots. Cook, stirring often, until the shallots are crispy and golden, about 5 minutes. Using a slotted spoon, transfer the shallots to a large plate lined with a paper towel and set aside. Remove the pot from the heat, but do not discard the oil.
6. Once the squash is tender, remove from the oven and scoop out the flesh directly onto the sheet pan. Discard the squash skins.
7. Return the Dutch oven with the shallot-infused oil to medium heat and stir in the reserved roughly chopped shallots, 3 garlic cloves, chopped, and 1 (1 1/2-inch) piece fresh ginger, peeled and chopped. Cook, stirring often, until tender and aromatic, about 4 minutes. 
8. Add the squash, roasted apple, and remaining 1/2 teaspoon fine salt to the Dutch oven along with 4 cups low-sodium vegetable broth. Bring the mixture to a boil over medium-high, then reduce the heat to medium-low and simmer, uncovered, until the flavors meld, about 20 minutes.
9. Carefully pour the mixture into a blender. Secure the lid and remove the center piece to allow steam to escape. Place a clean towel over the opening. Blend until thickened and smooth, about 1 minute.
10. Return the mixture to the Dutch oven and stir in 1 tablespoon apple cider vinegar and 1 1/2 teaspoons pure maple syrup.
11. Divide the soup evenly among 4 bowls and top with the reserved fried shallots and optional croutons, if making.

Cheesy Croutons (Optional)

1. Preheat the oven to 350 F. Line a small rimmed baking sheet with foil.
2. Toss 1 cup cubed sourdough bread with 2 tablespoons pre-grated parmesan cheese, 2 tablespoons olive oil, 1/4 teaspoon ground black pepper, and 1/4 teaspoon fine salt in a large bowl until well coated. Transfer to the prepared baking sheet and spread into an even layer.
3. Bake until toasted, stirring occasionally, about 20 minutes. Remove from the oven and let cool until ready to use.