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Fall is my favorite food season and it’s not because of holiday baking or pumpkin spice lattes. No, for me, it’s all about the warm and comforting flavors of things like winter squash, apples, and cinnamon and that’s what makes this Sausage Stuffed Butternut Squash my ideal autumn meal. (But really it fits in any time of year you’re able to find the squash.) It’s a master class in the balance of sweet and savory, thanks to a medley of complementary ingredients like salty Italian sausage, Honeycrisp apples, fragrant sage, maple syrup, fennel, and of course, that sweet butternut squash.

I love zucchini boats and stuffed bell peppers and the like – anytime you can stuff an entire meal into a vegetable, it makes it a little more fun. That’s definitely the case with this Stuffed Butternut Squash but it can feed quite a crowd; if you use two medium squashes, this can easily feed eight people!

You’ll just want to cut your squash in half and scoop out the seeds before you drizzle it with olive oil and season it with salt and pepper.

The squash then goes cut-side down on a baking sheet and bakes in a 425 degree oven until it’s tender.

While it bakes you can work on the filling, which has a fair amount of components but isn’t much trouble at all to make. You’ll start by browning up some bulk Italian sausage – hot or mild, it’s up to you.

You’ll remove the sausage from the skillet and then brown up some sliced fennel and onion, along with cubed Honeycrisp apples, some garlic, sage, and thyme. If you’re not a fan of fennel you can always skip it, but I think the anise flavor falls right into the sweet and savory blend here beautifully.

Once the squash has cooked and cooled enough to handle, you’ll scoop out some of the flesh, leaving a border around the edge and the bottom. If your squash is especially tender you can scoop it straight into the apple and fennel mixture, or you can chop it up first if it’s a little harder – the goal is to have small bites running throughout the mixture so either option works.

You mix the sausage and squash into the apple mixture and then pile it into the hollowed out squash.

A little dusting of grated Gruyere is all it needs before it heads back into the oven to brown up.

Oh, there’s a drizzle of maple syrup in that filling too, which might seem like it would get lost but in reality, is just the thing to tie everything together.

It’s such a great combination of fall flavors. The sausage is savory and a little spicy, and the fennel picks up the same anise flavor that it’s usually spiced with while the apple, butternut squash, and maple hit subtle sweet notes. The Gruyere cheese is just a little extra blanket of goodness, it adds some nuttiness and umami but doesn’t overpower everything else.

Serves 6-8

15m prep time

1h cook time

Rated 5 out of 5
Rated by 1 reviewers
  • 2 medium butternut squash
  • 1 lb bulk Italian sausage
  • 1 medium onion, thinly sliced
  • 1 fennel bulb, cored, halved, and thinly sliced
  • 3 cloves garlic, minced
  • 2 honey crisp apples, peeled, cored, and cubed
  • 1 tablespoon fresh sage, minced
  • 2 teaspoons fresh thyme
  • 1 tablespoon maple syrup
  • 1 1/2 cups Gruyere cheese, grated
  • Olive oil, as needed
  • Kosher salt and freshly ground black pepper, to taste
  1. Preheat oven to 425°F and line a baking sheet with parchment paper or aluminum foil.
  2. Slice each squash in half lengthwise, then scoop out the seeds and strings. Drizzle the flesh with olive oil, then season liberally with salt and pepper. Place face down on baking sheet and bake until tender, about 40 minutes.
  3. While squash bakes, add about a tablespoon of olive oil to a large skillet and set over medium heat. Crumble sausage into pan and cook until browned. Remove to a bowl and set aside.
  4. Add additional oil to skillet if needed, then add fennel and onion and cook until soft and golden, about 10 minutes. Add apples, garlic, sage, and thyme let cook a few minutes more.
  5. Drizzle with maple syrup, season with salt and pepper, then transfer mixture to bowl with sausage. Stir to combine.
  6. Once squash is tender, remove from oven and let cool enough to handle. Use a spoon to scoop out flesh, leaving a 3/4-inch border around the sides and bottom.
  7. Chop the squash you removed and add to bowl with sausage and apple mixture. (If squash is very tender, you can scoop it directly into the bowl without chopping.)
  8. Stir to incorporate squash, then spoon mixture into squash halves. Top with Gruyere cheese and more chopped sage, if desired. Bake until cheese is melted and bubbly, about 20 minutes. Enjoy!
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