Roasted Acorn Squash With Butter, Brown Sugar & Cinnamon

Tender and naturally sweet roasted acorn squash drenched with a buttery brown sugar and cinnamon sauce. A quick and easy crowd-pleasing holiday recipe!

Roasted acorn squash may not have been part of my mama’s fall kitchen table. Nor did it make an appearance at the Matthews’ house on Thanksgiving Day. However, this recipe is one that I discovered recently and would like to share with you.

This recipe features tender and naturally sweet roasted acorn squash drenched in buttery brown sugar and cinnamon sauce. I’m sharing this recipe with you today because it is a quick and easy crowd-pleasing recipe for the holiday season. I believe you need some simple recipes like this one to allow you to spend more time with your family and less time in the kitchen.

Roasted acorn squash will make your whole house smell warm and cozy, which is perfect when you have a whole bunch of folks coming over to entertain.

When I make this recipe David practically salivates when he smells the cinnamony goodness wafting out of the oven. However, when the squash is done, he will not touch them! Like a baked sweet potato, he says acorn squash tastes like “sweet dirt.” — Lord knows why he says that. I just let him be. It just means more for me and less to share.

Two Things To Remember When Making A Recipe For Acorn Squash 

Before I share this recipe with you, I want you to remember two things:

#1 Selection is very important!

When selecting an acorn squash, step away from the ones with too much orange on the outer skin. You need to run far away from them. The more orange an acorn squash becomes, the riper it is. Trust me; they will have a nasty stringy texture. It’s not anything you want to serve to anyone, not even your least favorite family members.

In addition, an acorn squash over three pounds is probably too ripe. It will have the same dry, stringy texture as an orangey one. Acorn squash should feel heavy for its size with smooth dull skin, free of spots and blemishes. 

#2 Always Roast Acorn Squash

Roasting is the best method for cooking an acorn squash because it intensifies the flavor and caramelizes the natural sugars in the squash.

These two points are based on my personal experience. If you are more selective with the acorn squash you purchase and always roast them whenever you need them for a recipe, you’ll do alright. 

You can read more about roasting pumpkin and winter squash HERE.

How To Make Roasted Acorn Squash With Butter, Brown Sugar & Cinnamon

Begin by preheating the oven to 375 degrees F. Line a baking sheet with aluminum foil or parchment paper; set aside.

Prepare the squash for baking:

Rinse the pumpkin and pat dry with paper towels.

Microwave the squash on high for about one minute before cutting. This will make the squash easier to cut into.

Next, cut the squash in half, sticking a heavy sharp knife down inside the squash. Push the blade down towards the bottom of the squash. 

Be sure to keep your fingers out of the way of the knife. Rotate the squash around so that you cut it all the way through. Sometimes they are tough to get open.  

A rubber mallet is helpful for tapping the knife through the squash. If the knife gets stuck, carefully give the squash a few firm whacks on the counter, until it releases the knife. Sometimes this will help the knife penetrate all the way through.

Spoon out the seeds and scrape the stringy pulp until the inside of the acorn squash half is smooth; discard the seeds and pulp. 

Season the squash:

Place the squash, cut side up, on the prepared baking sheet. Divide the butter in half and spread it inside each half of the squash. Then combine the brown sugar, and cinnamon in a small bowl and season with salt to taste. Sprinkle the brown sugar mixture inside of each squash half. 

Roast the Squash:

Roast the squash for 55 to 60 minutes, or until the top of the squash halves have a nice brown color and they are cooked through. The more you roast the more caramelized it becomes, so don’t worry about overcooking it. It’s better than an undercooked squash any day!

Serve the Squash:

Remove the squash from the oven and allow them to cool slightly. Baste the squash with any of the buttery brown sugar sauce that did not absorb into the squash before serving.

Hopefully, if you are looking for a last-minute side dish for your Thanksgiving table this will be the recipe you have been looking for. Never mind what David says.

I hope you enjoy them!