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Preheat the oven to 425 degrees. Brush the insides of the pumpkins with 2 tablespoons of melted butter and place them cut side down on the baking sheet. Arrange the pears cut side up around the pumpkin halves.
Bake pumpkins and pears, removing the pears when soft and lightly browned, after about 20 minutes. Continue roasting the pumpkins until a fork easily pierces all the way through (about 20 minutes longer).
Scoop the flesh out of the pumpkins and set aside in a bowl.
Melt remaining butter in a large pot or Dutch oven, over medium heat. Carefully add the sage leaves and fry until fragrant and crisp. Transfer the sage leaves to a plate lined with paper towels and set aside.
Add the onions and garlic to the remaining butter in the pot, and cook until softened, stirring occasionally (about 5 minutes).
Add the pumpkin and pears, along with the spices, stock, salt and pepper. Bring to a boil and simmer for about 15 minutes.
Remove from heat. Puree the soup with an immersion blender, or in batches in a regular blender and return to the pot. Stir in the heavy whipping cream and maple syrup. Taste and adjust the seasoning as necessary. If the soup is too thick, stir in a little more stock or water.
Ladle soup into bowls and garnish with a swirl of Greek yogurt, reserved crispy sage leaves and some roasted pepitas if desired.