Stuffed Winter Squash

November 19, 2020

For the holiday dedicated to stuffing things, I opt for a sweet winter squash as my centerpiece dish. Cooked to browned perfection and filled with a succulent stuffing, it’s been years since a turkey found its way to my table…and no one has missed it yet.

Makes 8-10 servings

Ingredient List:

  • 1 large winter squash, buttercup, hokkaido, hubbard work best
  • spring or filtered water
  • avocado oil

Corn Bread

  • 1 1/2 cups organic yellow corn meal
  • 1 cup sprouted whole wheat flour or whole wheat pastry flour
  • 2 teaspoons baking powder
  • 1 teaspoon baking soda
  • pinch sea salt
  • 2 tablespoons brown rice syrup
  • 3-4 tablespoons avocado oil
  • 1 cup spring or filtered water


  • 1 loaf sourdough bread, crusts removed and cubed
  • 1 recipe corn bread, cubed
  • 1 pound fresh/frozen chestnuts
  • spring or filtered water
  • 8 ounces tempeh, cut into tiny cubes and fried until golden
  • 1 teaspoon extra virgin olive oil
  • generous pinch dried rosemary
  • small handful fresh flat leaf parsley-minced
  • 2 cups spring or filtered water
  • organic soy sauce

Step By Step Instructions:

To begin, remove the top of the squash, jack-o-lantern style, so that you can scoop out the seeds and pulp. Replace the top and lightly oil the outer skin. Place in a baking dish with about 1/2-inch water. Bake at 325o, uncovered for about 25 minutes. Remove from oven and allow to cool while preparing the stuffing.

Prepare the corn bread by sifting together the corn meal, flour, baking powder/soda and salt. Whisk together the rice syrup, oil and water. Fold wet and dry ingredients together until just mixed. Do not over-mix or bread will be tough and heavy. Add a little more water if the batter seems too thick.

Preheat oven to 375o and lightly oil and flour a 9-inch square baking dish. Spoon batter evenly into pan and bake for about 30-35 minutes, until the top of the bread springs back to the touch. Invert on a wire rack and allow to cool before proceeding.

Cook’s Tip: The corn bread can be made a day ahead of time.

To prepare stuffing, preheat oven to 300o. Spread cubes of bread and corn bread evenly on a baking sheet and bake for about 20-30 minutes to dry. Set aside.

If using fresh chestnuts: Make a small slit in the flat side of each chestnut and place in a saucepan with water to cover. Simmer over medium heat until easily pierced with a knife, about 20 minutes. Remove from heat and taking 2-3 chestnuts at a time, peel off shells and skin. Set aside. If using frozen chestnuts, simply thaw them.

Heat oil in a skillet and sauté onions and rosemary, with a splash of soy sauce. Add celery, a splash of soy sauce and sauté until tender, about 8 minutes. Season lightly with soy sauce and remove from heat. Stir in chestnuts and fried tempeh cubes and transfer to a large mixing bowl.

Add bread and corn bread and mix well, slowly adding stock until stuffing forms a soft ball. Taste and adjust seasoning. If stuffing and baking the squash right away, then the stuffing can be hot when it goes into the squash. If you are making the stuffing ahead, then let it cool before proceeding.

Spoon the stuffing into the squash filling abundantly. Place the lid on the squash and return to baking dish. Add ½-inch water to the baking dish and cover with foil. Bake until squash pierces easily with a fork, 40 minutes to 1 hour. Remove foil and brown squash for 5-7 minutes. Allow to stand 10 minutes before slicing into wedges and serving.

Cook’s Tip: Any stuffing that doesn’t fit into the squash can be pressed into an oiled baking dish and baked until golden, about 30 minutes, and served on the side.