This is a tradition at our family during the October/November season when pumpkins are plentiful. The most important thing? Make sure the pumpkin can fit in your oven!!
I first found this recipe in a magazine several decades ago. I think Good Housekeeping. A few years back I found it online at a website that is defunct. It's reincarnated at the above link. Below is the recipe in its entirety.
1 pumpkin (7 lb.)
1 1/2 lb. garlic sausage
1 c. sliced sweet pepper
1 1/2 c. chopped onion
2 apples, cored and cubed
2/3 c. dry white wine
1/3 c. water
1/3 c. raisins
1 tsp. sugar
1/4 tsp. dried thyme
Preheat oven to 350 degrees. Cut top off pumpkin. Discard seeds and stringy pulp. Place pumpkin, cut side down, in a 13 x 9 x 2-inch baking pan. Fill pan with water to a depth of 1 inch. Bake pumpkin for 1 1/2 to 2 hours until tender. After pumpkin has been baking for 1 hour, prepare filling.
Cook sausage in a large skillet over medium high heat. Remove sausage and add peppers, onions and apples and thyme to skillet. Sauté until onions are transparent. Add wine, water, raisins, sugar and simmer 20 minutes.
Take pumpkin from oven. Discard water. Replace pumpkin, cut side up, in pan. Fill pumpkin with sausage mixture, mounding at the top, if necessary. Cover top with foil. Return to oven and bake for 10 minutes or until pumpkin and filling are heated. Serve directly from the pumpkin, scooping out pumpkin flesh to accompany each serving. Serves 6.
I normally serve the dish with rice.