Cornbread Dressing Stuffed Acorn Squash is the perfect carb and veggie hybrid for your Thanksgiving table. The individualized sizes serves as portion control so you have plenty of room left for pie.

If I could only choose one Thanksgiving side to serve alongside my turkey, it would have to be stuffing. (And honestly, I don’t even really need the turkey.) Whether it’s a traditional dressing, sweet and savory cornbread stuffing or a version full of untraditional ingredients, doesn’t really matter, but there better be some form of bread, onion, celery and chicken stock on my table, or the day could become very unpleasant, very fast.

Luckily, because Thanksgiving allows for a practically infinite amount of sides, I don’t have to choose just a few. I can have them ALL.

This particular side, Cornbread Dressing Stuffed Acorn Squash combines my very favorite side with my current favorite fall vegetable. It’s the perfect carb/veggie hybrid, which offers an individualized portion, so you don’t have to demonstrate any self-control, something I truly need otherwise I’d fill up on seconds and thirds, leaving me no room for pumpkin or pecan pie.

Aside from the innate portion control, this is also the perfect side if you’re serving a smaller crowd, anywhere from four to eight people. You could definitely duplicate the recipe as many times over as you want, but there’s something about miniature-sized dishes that doesn’t seem as practical for a large crowd.

Instead of slicing the squash down the middle, I actually chopped off both of the ends, so each piece could stand on its own without rolling, then hollowed out as much of the middle as I could. It makes for a more shallow depth so the stuffing to squash ratio is perfect in each bite.

Because squash has a longer cooking duration than the stuffing, I roasted them first while the stuffing was prepped. Each half of squash is brushed with a little bit of olive oil, plenty of salt and pepper, then places flesh-side down on a large baking sheet before they go into a super hot oven.

While that happens, a little bit of Italian sausage (I used chicken Italian sausage, but any variety will work well) is browned up and then sautéed with onion, celery and garlic. I stuck with tradition and simply seasoned the sausage and veggie mix with some salt, pepper, poultry seasoning and fresh sage before tossing the hot mixture with old cornbread, toasted sourdough, chicken stock and an egg. Oh, and we can’t forget, a little bit of melted butter too. It’s Thanksgiving, butter is allowed.

A quick seasoning check of salt and pepper is done before the stuffing/dressing is gently nestled into the mostly-roasted squash vessels.

The two items together cook for another 25-30 minutes until the stuffing is golden brown and crisp on the edges, and the squash is perfectly soft.

Garnish with a little bit of freshly chopped sage or flat-leaf parsley and this all-in-one side is ready for your holiday table.

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Cornbread Dressing Stuffed Acorn Squash

Course Side Dish
Cuisine American
Servings 6 people
Author Nicole

Ingredients

  • 3 acorn squash
  • 4 tsp olive oil, divided
  • 1 Italian sausage link, casing removed
  • 1/2 cup chopped celery
  • 1/2 cup diced onion
  • 2 tbsp minced sage
  • 3/4 tsp salt,divided
  • 2 cups cubed dried out sourdough bread (1/4-inch cube)
  • 2 cups crumbled cornbread
  • 1 tbsp unsalted butter, melted
  • 1/2 tsp poultry seasoning
  • 1/2 cup low-sodium chicken stock (plus more if you like)
  • 1 egg

Instructions

  1. Preheat oven to 400 degrees. Cut ends off of acorn squash, so you can stand both ends up straight. Cut in half. Try to make sure to leave enough of the end so there is a bottom for the stuffing to rest in.

  2. Brush the squash on all sides with three teaspoons of olive oil. Sprinkle with salt and pepper. Place flesh-side down on a large, rimmed baking sheet. Roast for 30 minutes. 

  3. While the squash roasts, make the stuffing. Add sausage to a medium non-stick skillet. Set on a medium-high heat and use a wooden spoon to break it up, cook until browned. Add a teaspoon of olive oil along with celery, onion, sage and 1/2 teaspoon salt. Saute until slightly softened, 5-6 minutes. 

  4. Add bread, cornbread, butter, poultry seasoning, chicken stock, egg, hot sausage, veggies and remaining 1/4 teaspoon salt to a medium bowl. Stir to combine. Season to taste with salt and pepper. 

  5. Once the squash roasts for 30 minutes, remove from the oven. Use a spatula to flip the squash over, then evenly divide the stuffing between the squash. Place back in the oven for another 25-30 minutes until the squash is soft and stuffing is crisp and golden brown. 

Cornbread Dressing Stuffed Acorn Squash