Brown Sugar and Cinnamon Baked Acorn Squash

Acorn squash is baked with olive oil, brown sugar, and cinnamon until tender and sweet for a delicious autumn and winter side dish. 

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Winter squash season has arrived again and I like to eat all different varieties. I actually love going to out local farm markets and seeing all the different shapes, colors, and sizes and trying them all whenever I see a new one.

This year I grew honeynut squash in my garden and it's one of my favorites. My ultimate favorite winter squash is delicata. However, acorn is a classic that I enjoy a lot, too.

I got a really large one at the farm market recently and knew it was time to update this very old post for brown sugar and cinnamon baked acorn squash. 

This is a pretty easy recipe and relatively straight forward. I like to bake acorn squash in wedges like this because it cooks faster than just cut in half, and it makes a better way to serve it out into portions. Half a large acorn squash can be a lot, especially for kids who may just want to try a smaller piece.

The acorn squash is washed, cut and cleaned and then placed in a baking dish as in the above photo. Then topped with brown sugar, seasonings, and olive oil and baked until tender.  

Acorn squash is not a very sweet winter squash. That is why I like to add a bit of brown sugar to it. Cinnamon always pairs nicely with an orange winter squash and with brown sugar making it all a delicious combination. 

This acorn squash pairs nicely with chicken, ham, or pork chops. You can add it to a salad if you'd like - one that is full of greens, dried cranberries, walnuts, apples, cheese, etc. would be lovely. 

I don't eat the skin of acorn squash. I find it to be too thick and not enjoyable to eat. Rather, I use my fork to scoop out the soft squash to eat and leave the skin. 

I'm always trying to find ways to make vegetables more appealing and enjoyable to eat. Adding a bit of spices, roasting or baking rather than boiling, making sure they still have some texture to them, and overall creating recipes we enjoy so that eating vegetables is something with want to do willingly. 

The only way I had acorn squash as a kid was pureed and full of a lot of butter and brown sugar. I never enjoyed the texture like that and for a long time I thought I didn't like it, along with other winter squash. 

Now, I know it's just a matter of finding ways to cook certain vegetables to get me to like them! Winter squash, Brussels sprouts, turnips, and others that I thought I didn't like are now things I eat much more frequently.   

While I used acorn squash in this recipe, you can use the same technique with other winter squash like carnival, butternut, or kabocha. 

If you find yourself with an acorn squash this fall or winter and are wondering how to use it, give this brown sugar and cinnamon baked acorn squash a try. 

Check out all the winter squash recipes on the blog for even more ideas to enjoy these vegetables.  

Yield: about 4 servings

Author: Amy B (Savory Moments)

Brown Sugar & Cinnamon Baked Acorn Squash

Acorn squash is baked with olive oil, brown sugar, and cinnamon until tender and sweet for a delicious autumn and winter side dish. 

Ingredients

• 1 medium/large acorn squash
• cooking spray
• 2 tablespoons brown sugar
• 1/2 teaspoon ground cinnamon
• 1/4 teaspoon freshly ground black pepper
• about 1 tablespoon olive oil
• salt, to taste

Instructions

1. Preheat the oven to 400 degrees.
2. Carefully cut the acorn squash in half lengthwise. Scoop out the seeds and clean out the cavity.
3. Cut each half into wedges (about 6 per half).
4. Lightly spray a large (9" x 11") baking pan with cooking spray. Arrange the acorn squash wedges in an even layer.
5. Sprinkle the brown sugar, cinnamon, black pepper, and a good pinch of salt over the squash. Drizzle with the olive oil.
6. Cover the pan with foil. Bake for 15 minutes. Turn the squash wedges over, cover again with the foil, and bake for another 15-20 minutes, until the squash is tender and easily pierced with a fork.
7. Taste and lightly sprinkle with more salt, if desired.

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I hope you give this brown sugar and cinnamon baked acorn squash recipe a try! Let me know in the comments below.

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This post was originally published in 2011 and has been updated in 2026 with new photos, new text, a recipe card and more to improve reader experience. 

Check out these other vegetable side dish recipes: 

Roasted Balsamic Radishes

Yellow Summer Squash Casserole 

Braised Red Cabbage with Cranberries & Maple 

Roasted Smoked Paprika Delicata Squash Sticks

White Cheddar Cauliflower Gratin