Roasted Acorn Squash with Cinnamon Sugar (“Squashies”)

I grew up eating what we called “groen pampoentjies” (little green pumpkins) almost weekly. My mom would boil pitted halves of little round gem squash, add butter, sugar and cinnamon and we would use the shell as a bowl and scoop out the deliciously sweetened flesh with a spoon. I loved it. I was told that “groen pampoentjies” would “make your hair grow pretty, healthy curls” and with it tasting as sweet as dessert, I had no qualms when it appeared on my dinner plate. When we arrived in the States, however, we quickly realized that gem squash was near impossible to find and so we quickly had to pivot and find a substitution to satisfy our craving. We quickly discovered that acorn squash would do the trick just fine (although it wasn’t quite the gem squash we knew and loved so much), and somewhere along the way, we began to call them “squashies.”

Years later in my own kitchen, when I began cooking squashies for my own family and friends, I adjusted the recipe to roast the squash instead of boiling it. Although boiling is a lot quicker and does make the flesh super soft, it also softens the shell so much that it can tear and then you lose your cute little bowl and the entire presentation! Additionally, I really like the more rustic texture and caramelization of the flesh that is achieved during the roasting process. Here’s how I prepare them:

You will need:

  • Acorn Squash
  • Butter
  • Sugar
  • Cinnamon

First, I slice the acorn squash in half lengthwise (do not try to slice through the stem, but rather break it off to one side or the other – let’s avoid any knife accidents while we’re at it!). With a spoon, I scoop out the seeds and guts and clean the flesh up until it’s smooth and I’ve gotten rid of any stringy fibers. If you’d like, you could set the seeds aside to roast – they make a delicious snack!

Once they are cleaned I place them on a baking sheet lined with parchment paper. I give the orange flesh a good brush with melted butter and slightly season with salt and pepper.

Once they’re seasoned, I flip them over (flesh side down) on the sheet and bake them at 350F for about 35 minutes. Some cooks prefer to roast acorn squash flesh side up, mainly to avoid having to flip them halfway through, but I prefer this way as it creates some delicious caramelization on the rim of the squash.

After 35 minutes, I remove them from the oven, flip them over (flesh side up) and return to the oven for 15 more minutes. At this point, you should be able to see the caramelization on parts of the rim. While they roast, I mix together the cinnamon and sugar as I will need it in the next step.

After the second roasting time, remove the squash from the oven and sprinkle with the cinnamon sugar, dividing it between the four halves. I add a pat of the remaining butter to the middle of each shell and return them to the oven, turning it up to broil for 5 more minutes. This lets the cinnamon sugar mixture and butter melt into the flesh a little and releases that delicious aroma of Fall and coziness that warm cinnamon creates so well.

I usually serve these immediately, in the shell, and mix up the flesh, cinnamon sugar, and butter before taking a bite. It is a delicious addition to any Fall meal, and could even be a showstopper-side-dish on your Holiday menu.

Roasted Acorn Squash with Cinnamon Sugar (“Squashies”)

Prep Time 10 minutes
Cook Time 55 minutes
Course Side Dish
Cuisine South African
Servings 0

Ingredients
  

  • 2 Acorn Squash
  • 4 tbsp Butter (plus extra melted butter for brushing)
  • 2 tbsp Sugar
  • ¼ tsp Cinnamon
  • Salt & Pepper

Instructions
 

  • Preheat the oven to 350℉.
  • Cut the squash in half lengthwise and scoop out seeds and guts with a spoon, making sure to clean the flesh until all stringy fibers have been removed.
  • Place the squash halves on a lined baking sheet, brush the (extra) melted butter on the flesh, and season slightly with salt and pepper.
  • Flip the squash flesh-side down and roast in the preheated oven for 35 minutes.
  • Remove from the oven, flip the squash over (flesh-side up) and return to the oven for an additional 15 minutes. While roasting, mix together the cinnamon and sugar and divide the butter into four pats.
  • Remove the squash and sprinkle with the cinnamon sugar, dividing it between the four squash halves. Add a pat of butter in the hollow of each squash and return to the oven, switching to broil, for 5 more minutes.
  • Serve immediately in the shell and mix some of the seasonings butter and squash flesh with a fork before taking a bite.
Keyword Acorn Squash, Fall, Roasted Squash, Side Dish
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