Cranberry Apple Stuffed Acorn Squash Recipe

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.

white serving platter with stuffed acorn squash

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 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.

This stuffed acorn squash recipe is incredibly easy to whip up – just a few ingredients and super simple prep. Perfect for the busy holiday season!

Ingredients you’ll need

Here is a visual overview of the ingredients in the recipe. Scroll down to the recipe at the bottom for quantities.

ingredients for apple stuffed acorn squash with text labels — Ingredients for Cranberry Apple Stuffed Acorn Squash: Acorn squashes, apples, apple juice, dried cranberries, brown sugar, pecans, cinnamon, salt, cornstarch and butter.

Ingredient notes

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.

How to make stuffed acorn squash

Start by cutting and de-seeding the squashes, then cut them in half lengthwise and roast them in the oven until tender.

While the squash is roasting, make the filling. Place the cranberries in a pot with the apple juice and spices (1), then bring to a boil with the brown sugar (2).

steps to show making apple filling for acorn squash

Once the cranberries are soft and plump, stir in the cornstarch slurry (3) and simmer until thickened (4).

Finally, add the apples, pecans and butter (5) and stir through (6).

Once the squash is roasted (7), carefully flip the halves over, divide the filling between them and bake for another 5-10 minutes.

collage to show how to fill acorn squash halves

Recipe tips

Pick good squashes: Since the squash is the main part and serving vehicle of this dish, it’s wise to pick some nice ones. 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!

three stuffed acorn squashes on a white platter

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.

platter with stuffed acorn squash from overhead view

Recipe FAQs

How do you cut and cook acorn squash?

To make stuffed acorn squash, you only have to rinse the squash, cut it in half lengthwise 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 may not have quite cooked through by then, but that’s fine because it will bake for another 5 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.

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.

How long to bake stuffed acorn squash:

The squash needs to bake for 30 minutes by itself before you can add the filling. Once you have filled the squash halves, they go back in the oven for around 5-10 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.

stuffed acorn squash in a white bowl with a fork

Serving ideas

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!

More easy holiday sides

PS If you try this recipe, please leave a review in the comment section – I appreciate your feedback! Follow along on Pinterest, Facebook or Instagram. Sign up for my email list, too!

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

Cranberry Apple Stuffed Acorn Squash