Toss squash, bell pepper, and garlic in olive oil and season generously with salt and pepper. Cover a baking sheet with parchment paper and arrange vegetables in a single layer, being sure to put the pepper cut side down. Roast 25 minutes, or until squash is tender and bell pepper begins to char.
Transfer to pot over medium high heat. Add chicken stock and blend with immersion blender until smooth.
Add remaining ingredients and let simmer 20 minutes, stirring occasionally. Taste and add salt and pepper if needed. Remove bay leaf before serving. Garnish with a drizzle of heavy cream and a sprinkle of roasted pumpkin seeds for a crunch.