Preheat oven to 375° F.
Use a sharp knife to remove the top of the pumpkin in one piece then set aside. Remove the pumpkin seeds and flesh of the pumpkin using a spoon or scoop. Make sure you got everything inside of the pumpkin. Replace lid on pumpkin.
Place the pumpkin on a lined parchment paper baking sheet. Bake it at 375° F for approximately 45 minutes until slightly softened. (Note: The time will depend on actual size of the pumpkin). Remove from heat and carefully remove lid and set aside to cool slightly.
Meanwhile while the pumpkin is roasting, toast the walnuts in a dry, small skillet for 5-6 minutes over medium-high heat. Do this until it's fragrant. Stir often and watch carefully to prevent burning. Remove from heat and set aside.
Put a drizzle of olive oil on a large skillet in medium heat. Add the onions. Cook by stirring occasionally until onions become slightly soft and translucent.
Add the diced chicken and sauté until golden brown.
Add garlic, tomato puree, and the cup of water. Cover skillet with a lid and simmer over low heat for approximately 20 minutes.
Ladle filling into pumpkin. Add the chopped walnuts, herbs, and cherry tomatoes, reserving a few for garnish. Season with a teaspoon salt and teaspoon pepper or adjust according to taste.
Return pumpkin to oven and roast for another 20-25 minutes. Serve warm on a large plate. Enjoy!