Get ready. Preheat the oven to 425°F and arrange two racks in the top and bottom thirds.
Prepare the vegetables. Place the butternut squash halves cut-side up on a sheet pan. Brush with 1 tablespoon olive oil and sprinkle with salt. Place the apples skin-side up on a second sheet pan and scatter the sliced fennel on, too. Drizzle the apples and fennel with the tablespoon of olive oil and sprinkle with salt.
Roast the vegetables. Transfer both pans to the oven. After 15 minutes, toss the fennel and rotate the pans. After another 15 minutes (30 minutes total), once the apples and fennel are caramelized and golden, remove them from the oven. Continue roasting the squash until fork-tender and charred in spots, about 20 to 30 minutes longer.
Purée the vegetables. Scoop the roasted squash flesh out of the skin and into a blender. Add the roasted apples, fennel, vegetable broth, and a pinch more salt. Blend until smooth, working in batches if needed. (Alternatively, use an immersion blender.)
Simmer and season. Transfer the vegetable puree to a pot. Add the Aleppo pepper, apple cider vinegar, and black pepper, and simmer gently for 5 to 10 minutes to reheat and let the flavors come together. Adjust seasoning to taste.
Garnish and serve. Ladle into bowls and top with roasted pepitas, a sprinkle of Aleppo pepper, and a drizzle of extra virgin olive oil. Serve.
Notes
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