Cranberry Apple Stuffed Acorn Squash

Cranberry Apple Stuffed Acorn Squash is the perfect harvest inspired side dish. The pecans make for a nice crunchy topping – perfect for Thanksgiving or Christmas dinner-

I’m so much into holiday side dishes – I could happily pass on the turkey and feast only on the (buttery, cheesy, carby) side dishes.

And even outside of holiday dinners – coziness is always welcome. I’ll happily eat my wild rice salad and Cozy Pumpkin Cornbread and Stuffed Acorn Squash and cuddle up in my furry blanket in front of 13 Going on 30 Mean Girls Twilight I mean the news.

How to make my apple stuffed acorn squash recipe:

Read on for the detailed step-by-step instructions, or scroll down for tips and the printable recipe card.

Ingredients to Make Stuffed Acorn Squash:

• acorn squashes
• apple juice
• brown sugar
• dried cranberries
• ground cinnamon
• ground nutmeg
• salt
• cornstarch
• butter
• apples
• chopped pecans

I guess you can fill pretty much every winter squash – small butternuts would be a great substitute for the acorn squashes. But even baby bear pumpkins would be delicious!

If you don’t want to add any sugar, use maple syrup or honey in place of the brown sugar. You may need to add an extra tablespoon or two, but make sure to taste the filling first and go according to taste.

Chopped walnuts are a great substitute for the chopped pecans. Use pepitas if you want to avoid nuts!

This is a tasty vegetarian side dish, but to make this heartier, add browned sausage meat to the filling.

To make this vegan, use coconut oil or vegan margarine in place of the butter. It will change the taste a little, but it will still be delicious.

Key Steps to the Best Stuffed Acorn Squash:

• Pick a good squash: Since the squash is a pretty main part of this dish, it’s wise to pick a nice one. I’ve found the best acorn squashes for stuffing are firm ones on the smaller side.
• Thicken the sauce enough: It shouldn’t take longer than two minutes, but do make sure the sauce coats the filling like jam – if it’s still too liquid, it will make the dish soggy. Add more cornstarch slurry to make it thicker.
• Season to taste: I like adding just some cinnamon and nutmeg, but it’s also delicious with pumpkin spice or even some vanilla!

1 Roast the Squash

How do you cut and cook acorn squash?

To make stuffed acorn squash, you only have to rinse the squash, cut it in half and scoop out the seeds. Easy!

To cook it, we’re roasting it in the oven: Place the squash cut side down on a lightly greased baking sheet, then bake it for around 30 minutes.

It will not have quite cooked through by then, but that’s fine because it will bake for another 15 minutes with the filling.

Is skin of acorn squash edible?

It is, and roasting it for a long time will make it softer and easier to eat.

If you’re like me and not a huge fan of eating the skin… Don’t worry: The flesh easily separates from the skin, and you can eat the flesh away as if the skin was a bowl.

2 Make the Filling:

Do I cook the stuffing first for acorn squash?

In short: Yes, you cook the filling or stuffing first, then add it to the almost-baked squash and finish roasting the two together.

Making this filling is super easy: You’ll cook the dried cranberries in apple juice, brown sugar and spices to rehydrate them. Then thicken the juices with a cornstarch slurry and finally stir in chopped apple and pecans.

This will create a really delicious filling for your squash, with a much better consistency than not cooking it first.

3 Fill the squash:

Finally, carefully remove the acorn squash from the oven and flip it (seriously, careful – they are hot!).

Then spoon the filling into the hollows where you scooped out the seeds.

How long to bake stuffed acorn squash:

Once you have filled the squash halves, they go back in the oven for around 15 minutes.

You can easily check the acorn squash for doneness by carefully sticking a fork or a sharp knife into the thickest part – it should be very soft all the way through.

Make Ahead Instructions:

It’s always good to be able to make ahead the dishes for a holiday meal. And this one works great!

You can roast the squash up to a day ahead. Cool it to room temperature, then place it in a deep baking dish and cover it with foil. Refrigerate until ready to use.

Make the filling up to a day ahead, too, but DO NOT add the apple and pecans yet. The apples would turn brown, the pecans would soak up all the liquid and turn soft. Let the filling cool to room temperature, then cover and refrigerate.

When ready to bake, chop the apples and pecans and stir them into the prepared filling. Spoon into the prepared squash and bake in the preheated oven for around 20-25 minutes, or until the squash is soft and the dish is hot all the way through.

How to Serve Stuffed Acorn Squash:

This is such a nice side dish – and it works for so many occasions, not just Thanksgiving!

Actually, I love making it for lunch on any random day – it’s quick and easy, full of seasonal produce and both my kids love it. It tastes great with breakfast sausage for a special brunch, too!

Here are some of our favorite mains to have this squash with:

Get the printable recipe for this stuffed acorn squash:

More holiday side dishes:

This recipe was first published on Food Fanatic as Cranberry Apple Stuffed Acorn Squash Recipe.