Preheat oven to 425ºF. Place the halved squash on an aluminum foil lined baking sheet. Melt 1 tablespoon of butter and brush all over the cut sides of the squash. Season with 1/2 teaspoon of kosher salt and 1/4 teaspoon pepper. Roast for 1 hour - 1 hour 15 minutes, or until squash is very tender all the way through. Set aside to cool enough to handle.
Peel, core and chop one of the apples. Melt 1 tablespoon butter in a large saucepan and add apple, onion, and sage. Cook, stirring occasionally, about 7 minutes or until softened. Remove from heat.
When squash is cool enough, scoop it out of the skins and add roasted squash to the large saucepan with apples and onions. Discard skins. Add the broth, cider, water, brown sugar, 1/2 teaspoon kosher salt, 1/4 teaspoon pepper, and pinch of cayenne pepper.
Bring to a boil over medium-high heat, breaking up chunks of squash. Reduce heat and simmer uncovered, stirring occasionally, about 15 minutes. Remove pan from heat and stir in half and half. Using an immersion blender blend soup in pan until smooth.* Taste and adjust seasoning with more salt, if necessary.
Core and chop remaining apple. Melt 1 tbsp. butter in skillet and sauté chopped apple 7-9 minutes, stirring occasionally, until golden and soft. Top soup with yogurt and sautéed apples.
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*If you don't have an immersion blender, carefully pour hot soup in blender and process until smooth.Suggested Toppings for Roasted Butternut Squash Soup
Sautéed Apples - chop up an apple and sauté in butter
Sprinkle on Cinnamon
Dollop with yogurt
Crispy bacon or prosciutto
Nuts such as candied pecans, walnuts, or pepitas
Cheese - try sharp cheddar, feta, or goat cheese
Can Butternut Squash Soup Be Frozen?Yes, it can. However, when it thaws I find the soup to be thinner than when it was first made.To avoid this, omit the cream before freezing. When you are ready to serve, thaw, reheat and add the cream to reach desired thickness.Adapted from Chowhound