1/4 teaspoon freshly ground black pepper, plus more as needed
1/3 cup heavy cream
1/2 cup toasted pumpkin seeds, for garnish (optional)
The Build
Heat the oven to 425°F and arrange a rack in the middle. Line a baking sheet with aluminum foil. Place the squash pieces cut-side up on the baking sheet. Melt 1 tablespoon of the butter and brush all of it over the tops and insides of the squash halves (alternatively, you can rub it on evenly with your fingers). Season generously with salt and pepper. Roast until knife tender, 50 minutes to 1 hour.
Meanwhile, peel, core, and cut the apple into medium dice. Cut the onion into medium dice. Melt the remaining tablespoon of butter in a large saucepan or Dutch oven over medium heat. Add the apple, onion, and sage, season with salt and pepper, and cook, stirring occasionally, until softened, about 7 minutes. Ad crushed garlic to the pot for the last 30-45 seconds of the saute. Remove the pan from the heat and set aside.
When the squash is ready, set the baking sheet on a wire rack until the squash is cool enough to handle. Using a large spoon, scoop the flesh into the saucepan with the sautéed apples and onions; discard the skins.
Add the broth, water, and measured salt and pepper, stir to combine, and bring to a boil over medium-high heat. Reduce the heat to medium low and simmer, stirring occasionally and breaking up any large pieces of squash, until the flavors meld, about 15 minutes. Remove the pan from the heat and stir in the cream.
Using a blender, purée the soup in batches until smooth, removing the small cap (the pour lid) from the blender lid and covering the space with a kitchen towel (this allows steam to escape and prevents the blender lid from popping off). Alternatively, use an immersion blender. Taste and season with salt and pepper as needed. Serve garnished with the pumpkin seeds, if using.