Roasted Acorn Squash with Cinnamon Sugar

Roasted Acorn Squash with Cinnamon Sugar (“Squashies”)

Growing up, we ate what we called groen pampoentjies — little green pumpkins — almost every week. My mom would boil gem squash halves, scoop out the seeds, and serve them right in their shells with butter, sugar, and cinnamon. I loved it. We were told they’d “make your hair grow pretty, healthy curls,” and since they tasted like dessert, I never complained when they showed up on my plate.

After moving to the States, we realized gem squash is nearly impossible to find, so we had to pivot. Enter: acorn squash — not quite the same, but close enough to satisfy the craving. Somewhere along the way, we started calling them “squashies.”

Why I Roast Instead of Boil

While boiling is faster and makes the flesh ultra-soft, it also weakens the shell — and I love serving these in their little “bowl.” Roasting not only keeps the shape intact, but it also caramelizes the edges and deepens the flavor. Rustic, golden, and full of fall comfort.

You will need:

• Acorn squash (2 medium-sized)
• Butter
• Sugar
• Cinnamon
• Salt and pepper

How I Make Squashies

I start by slicing the acorn squash in half lengthwise. I never cut through the stem — instead, I break it off to one side to keep things safe and easy. Once halved, I scoop out the seeds and stringy bits with a spoon until the inside is clean and smooth. If I have time, I’ll set the seeds aside to roast later as a snack.

Once cleaned, I place the squash halves cut side up on a parchment-lined baking sheet. I brush the orange flesh generously with melted butter and sprinkle lightly with salt and pepper. Then I flip them over so they’re cut side down, and roast them in a 350°F oven for about 35 minutes. This helps caramelize the edges and keeps the squash tender but not soggy.

After that first roast, I flip them back over — cut side up — and pop them back in for another 15 minutes. While they’re finishing up, I mix together the cinnamon and sugar so it’s ready for the final step.

When the squash comes out again, I sprinkle each one with the cinnamon sugar, add a small pat of butter to the center, and slide them back in under the broiler for about 5 minutes. This melts the butter and sugar right into the flesh and fills the kitchen with the coziest fall scent imaginable.

Serving Tips

I serve squashies warm and right in the shell. The butter and cinnamon sugar get stirred right into the soft golden flesh with each bite. It’s nostalgic, comforting, and just special enough to earn a spot on a holiday table — but simple enough for any weeknight in fall.