Heat the canola oil in a small stockpot until shimmering and add the onion and garlic. Stir and sauté until the onion is tender and begins to color, about 10 minutes.
Add the diced pumpkin and stir well. Continue to sauté another 5 minutes while the pumpkin begins to soften.
Add the ground pork and stir well. Cook until ¾ of the pork is white.
Add the dried spices and the minced chipotle chile. Stir and sauté a couple minutes until the onions and pork are coated with the spices.
Add the tomatoes, cherries and water and bring to a boil. Lower heat and simmer 30 minutes until the pumpkin is tender and the chili has reduced and thickened.
Preheat oven to 350°F.
Meanwhile, cut the top third from the pie pumpkins and remove the seeds.
Brush the insides of the pumpkins with a little olive oil and season with salt and pepper.
Bake the pumpkins and the tops on a foil-lined baking sheet for 30 minutes until tender, but not collapsed. Pumpkins may be baked the day before and re-warmed in the microwave.
Spoon the chili into the pumpkin shells and replace the pumpkin top. Serve immediately. These pumpkins will stay hot on a buffet for 30 minutes. Provide a broad spatula for guests to help themselves.