Cut squash in half. Remove and discard seeds and stringy flesh from squash. Drizzle the cavity of the squash with olive oil and salt and pepper. Place the squash cut side down on a rimmed baking sheet that has been lined with parchment paper or foil and roast for 30-40 minutes, or until the flesh if fork tender. The variation in cooking time is due to the size of the acorn squash. It is best to test the squash with a fork to determine if it is done or not.
Heat a dutch oven (or large skillet that can be covered) over medium high heat. Add in the sausage, and begin to brown. Once the fat begins to render off the sausage, add in the onion and celery. Saute until the sausage is browned and cooked through, being sure to break up the sausage into small chunks as it cooks. Drain off excess fat if desired and return pan to the heat.
Stir in the rice and let toast for 30 seconds to one minute. If using, add in the white wine and simmer until the wine has mostly evaporated. Stir in the stock, salt, pepper, sage, thyme leaves and cranberries. Bring mixture a boil and then reduce heat to a simmer. Cover and cook for 45 minutes, or until rice is tender. Remove from heat and stir in apples.
Stuff the filling into the roasted acorn squash.
Return to the oven for 10-15 minutes to warm everything through together.
I used Lundberg Wild Rice Blend. For every 1 cup of rice, 1 3/4 cups of liquid is needed and it has a cook time of 45 minutes. If you select another grain/rice blend, follow the liquid to grain ratio and cook time suggested on the package. For a dry white wine, use a Sauvignon Blanc or Riesling. It is also fine to omit the wine, it is only added for extra depth of flavor. Feel free to omit sage if your family does not care for the flavor. For VEGAN Stuffed Acorn Squash, omit the sausage from this recipe.For Paleo Stuffed Acorn Squash, use 2 pounds of sausage and omit the rice and dried cranberries. Store leftover Stuffed Squash for 3 days in the fridge. This recipe can also be prepared in advance and then frozen for up 3 months. Simply remove stuffed squash from the freezer, and bake covered at 350 degrees for one hour, or until warmed through. Nutrition is an estimate. It will vary based on sausage and grain used.