Skip to Content

Roasted Acorn Squash with Crispy Prosciutto

Sharing is caring!

This Roasted Acorn Squash with Crispy Prosciutto is a delicious and memorable side dish.

I love acorn squash, and this Roasted Acorn Squash is a perfect holiday side dish. The squash is roasted until it is almost caramelized and it is topped with crispy prosciutto. It is the ultimate combination of sweet and salty flavors and it paired wonderfully with my Honey Maple Glazed Ham.

In the past when I made acorn squash, I sliced it in half, scooped out the seeds, and roasted it. This time around I sliced the squash into one inch pieces, and I think that it made the final result even better. This way the squash absorbed even more of the butter, maple syrup, and brown sugar.

I roasted the squash for an hour, until it was soft. It just needs to be flipped once, so this is a no fuss side dish. It does reheat well, so you can prepare the squash in advance and then reheat it. Leftover squash is a nice addition to a spinach salad.

You can eat the skin of the squash, but it does peal off pretty easily after the squash has been roasted. Peeling a raw squash is a tedious process that I do not recommend.

If you have been reading this blog for a while, you might have picked up on my obsession with crispy prosciutto. I think it is even better than bacon. It is thinner and crunchier, and a bit saltier. You could use bacon if you prefer. The trick to keeping the prosciutto nice and crispy is to add it to the top of the squash just before serving.

I served this roasted acorn squash with Maple Honey Glazed Ham, Creamy Spinach, and a savory Caramelized Onion, Pear, and Blue Cheese Galette. It was a more modern and sophisticated take on a holiday menu. You could opt to serve the squash instead of, or in addition to mashed potatoes.

One trick to roasting vegetables is to line the baking sheet with parchment. This helps the vegetables to cook more evenly. I do this for all vegetables, not just squash. Parchment paper also makes for easy clean up – something that is a huge timesaver when you are preparing a holiday meal.

Roasted Acorn Squash with Crispy Prosciutto

15 minPrep Time

1 hrCook Time

1 hr, 15 Total Time

Save RecipeSave Recipe


  • 2 Acorn Squash
  • 1/4 cup Melted Butter
  • 2 tablespoons Maple Syrup
  • 4 tablespoons Brown Sugar
  • 1 teaspoon Salt
  • 3 slices of Prosciutto


  1. Heat your oven to 350 degrees.
  2. Slice each squash in half, scoop out the seeds, and then slice the squash into half circles that are about an inch and half thick. Spread them out on a parchment lined baking sheet.
  3. Whisk the melted butter, maple syrup, salt, and 2 tablespoon brown sugar together. Brush the mixture over the squash (there will be a little leftover - set aside for later). Roast the squash for 40 minutes.
  4. Remove the squash from the oven, and flip it over. Brush the remaining butter mixture over (reheat it in the microwave to get the butter to melt again). Sprinkle the squash with the remaining brown sugar. Return to the oven for 20 minutes.
  5. Spread the prosciutto out on another parchment lined baking sheet. Let cook for 12-15 minutes, until it has hardened. Then remove from the oven and let cool.
  6. Once the squash is done roasting, place it in a serving dish and crumble the prosciutto over the top.

Want to save this Roasted Acorn Squash with Crispy Prosciutto recipe for later? Here is an image for you to pin?

Roasted Acorn Squash is a perfect holiday side dish

Roasted Carrots, the Easiest Side Dish Story How to Make Cheesy Grits Story Enchiladas Suizas Grilled Cheese Story 13 Creative Ways to Use Leftovers Story Buffalo Chicken Meatballs Story