Preheat oven to 375 degrees.
Wash pumpkins thoroughly, cut off tops, and remove seeds & membranes.
Place pumpkins on a large baking dish. Using one tablespoon of olive oil brush insides of each pumpkin and sprinkle with 1 teaspoon of salt and a ½ teaspoon of black pepper.
Cover with aluminum foil and bake for 30-35 minutes or until fork tender.
While the pumpkins are in the oven, prepare filling. In a large cast iron skillet add 1 tablespoon of olive oil and begin browning sausage over medium-high heat. Break up the sausage using your spatula as it cooks.
Once sausage has begun to brown add the shallots, garlic, 1 teaspoon of salt, ½ teaspoon of pepper, and sage. Cook another 2 minutes or until sausage is cooked through (no longer pink) and onions & garlic have become aromatic.
Pour white wine into skillet and scrape brown bits from bottom with a spatula. Cook until most of the liquid has evaporated.
Add sliced mushrooms to the skillet. Cook 5-7 minutes over medium-high heat or until mushrooms begin to brown and release most of their moisture.
Next, add baby spinach and cook until wilted, approximately 3-4 minutes.
Once spinach has wilted, add cranberries and pecans to sausage mixture, stir to combine.
Fill each pumpkin with sausage filling.
Place pumpkins back in oven, uncovered, and continue to bake for 5 minutes or until heated through.
Remove from oven and sprinkle with parmesan cheese.