Stuffed Acorn Squash with Cranberries & Brussels Sprouts

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Stuffed Acorn Squash, filled with roasted brussels sprouts & cranberries, is a flavorful, beautiful dish. This recipe is also easy to make, healthy, gluten free & whole 30 approved!

Make it as a main dish for a delicious fall dinner or serve it as a side dish with your Thanksgiving or holiday meal!

stuffed acorn squash half filled with roasted brussels sprouts and cranberries

It’s Thanksgiving Week y’all! My favorite week of the year where I share delicious main dishes, side dishes and desserts for your Thanksgiving or Friendsgiving meal.

Let’s check out what’s on the menu this year!

If you’re looking for a tasty Thanksgiving appetizer, check out this Butternut Squash Bruschetta. And for a delicious cocktail, check out this Cranberry Apple Sangria. For even more Thanksgiving inspiration, check out my Top 15 Thanksgiving Recipes. I update this list every year to include the MOST POPULAR recipes on the blog for Thanksgiving dinner!

When it comes to side dishes, I love traditional stuffing and mashed potatoes, but I like mixing up the vegetable sides each year. This roasted acorn squash, filled with brussels sprouts, cranberries and pancetta is a GORGEOUS side dish to serve at Thanksgiving dinner. And you never have to tell anyone how easy it was to make!

Simply roast the squash on one sheet pan and the filling on another sheet pan. Remove both from the oven and spoon the filling into the squash. Voila, a simple, beautiful side dish is served!

This stuffed acorn squash recipe is also perfect for those with dietary needs around the holidays. It’s already gluten free, dairy free and whole 30 approved. And it’s very easy to make vegan by simply omitting the pancetta.

In addition to being the perfect side dish for a holiday meal, this stuffed acorn squash is also a delicious main dish for weeknight dinners during the fall and winter months. It only takes 10 minutes to prep, so your hands-on time is minimal and the result is a healthy, delicious dinner! Friends and family will love this recipe no matter when you serve it, I guarantee it!

Roasted acorn squash stuffed with brussels sprouts and cranberries

How to make Stuffed Acorn Squash

  • Roast the acorn squash.

    • Slice the acorn squash in half.
      • Quick tip! I recommend using an electric knife to easily slice the uncooked squash in half.
    • Remove the seeds from inside the squash. I like to use a fork to easily scoop out the seeds and discard them.
    • Brush the inside of the squash with olive oil or use an olive oil cooking spray to spray the squash with olive oil.
    • Sprinkle salt and pepper on the inside of the squash.
    • Place the squash halves cut side down on a parchment paper or foil lined baking sheet.
    • Roast the squash in a 350°F oven for 30 minutes.
  • Prepare the acorn squash filling.

    • Spread halved brussels sprouts in an even layer on another sheet pan lined with foil.
    • Add minced garlic, diced pancetta and fresh cranberries to the sheet pan with the brussels sprouts.
    • Drizzle olive oil and balsamic vinegar over the brussels sprouts, then sprinkle with salt and pepper.
    • Stir to combine everything on the sheet pan.
    • Roast in the oven with the acorn squash at 350°F for 20-25 minutes.
  • Finish the dish.

    • Remove the roasted acorn squash and brussels sprout filling from the oven.
    • Spoon the brussels sprout filling into the acorn squash and serve.

Instructional images how to make roasted brussels sprout stuffed acorn squash

Common substitution questions for this recipe

  • What can I substitute for pancetta? Diced thick cut bacon can be substituted for pancetta in this recipe.
  • Can I use dried cranberries in this recipe? I love the flavor and texture that fresh cranberries bring to this recipe, but if you can’t find fresh cranberries, dried cranberries can be mixed into the brussels sprout filling after it’s roasted. Frozen cranberries can also be used in place of fresh cranberries with no change to the roasting time.

Can you eat acorn squash skin?

Yes, the skin of the acorn squash is totally edible. If using a small enough acorn squash (1-2 pounds in size), after roasting the squash, the skin should be tender enough to eat.

It’s totally a personal preference though. I’m not a huge fan of the texture of squash skin, so I generally don’t eat it, but it is absolutely edible and safe to eat.

What does acorn squash taste like?

If you’ve never tried acorn squash, you might be wondering what it tastes like compared to other squash varieties. Acorn squash is slightly sweet, but not as sweet as butternut squash.

It’s mild in flavor and, when roasted, has a texture somewhere between a butternut squash and spaghetti squash. It’s not as smooth as butternut squash, but not as stringy as spaghetti squash. Because of its mild flavor, it pairs well with strong flavors like brussels sprouts!

Fun fact! Acorn squash is actually the most nutritious of all the squashes. It’s high levels of folate, calcium, magnesium, and potassium make it a wonderfully healthy option!

What to serve with Stuffed Acorn Squash

This stuffed acorn squash can easily be served on it’s own or as a side dish. If serving on it’s own, I recommend one whole stuffed squash per person. If serving it as a side dish, I recommend one half stuffed squash per person.

When serving Stuffed Acorn Squash as a side dish, it pairs well with roasted, grilled and smoked meats, like turkey, pork or steak. Here are a few recipes to try with this roasted acorn squash recipe:

Stuffed acorn squash halves on plate filled with roasted brussels sprouts and cranberries

Making this gorgeous stuffed acorn squash for dinner or a holiday meal? I’d love to see it! Be sure to share a pic on Instagram and tag me @WhitneyBond on your feed or story!

Made it and loved it? Please be sure to rate the recipe in the box below!

Roasted acorn squash halves, filled with brussels sprouts, cranberries and fresh rosemary
5 from 3 votes
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Stuffed Acorn Squash with Cranberries & Brussels Sprouts

Stuffed Acorn Squash, filled with roasted brussels sprouts & cranberries, is a flavorful, beautiful dish, that's also easy to make, gluten free & whole 30 approved!

Course Main Course, Side Dish
Cuisine American
Prep Time 10 minutes
Cook Time 30 minutes
Total Time 40 minutes
Servings 4 stuffed squash halves
Calories 228 kcal
Author Whitney Bond

Ingredients

  • 2 acorn squash 1-2 lbs in size
  • 3 tbsp olive oil divided
  • 1 tsp kosher salt divided
  • 1 tsp black pepper divided
  • 3 cups brussels sprouts halved or quartered
  • 3 cloves garlic minced
  • ¼ cup pancetta diced
  • ½ cup fresh cranberries
  • 2 tbsp balsamic vinegar

Instructions

  1. Preheat the oven to 350°F.

  2. Slice both acorn squash in half.

  3. Remove the seeds and brush the insides of the acorn squash with 1 tbsp olive oil.

  4. Sprinkle ½ tsp salt and ½ black pepper across the insides of the acorn squash.

  5. Place the squash cut side down on a foil or parchment lined baking sheet.

  6. Place in the oven to roast for 30 minutes.
  7. On another baking sheet, lined with foil, spread the brussels sprouts out in an even layer

  8. Add the garlic, pancetta and cranberries.
  9. Drizzle with the additional 2 tablespoons of olive oil and the balsamic vinegar.

  10. Sprinkle the remaining ½ tsp salt and ½ tsp black pepper on the brussels sprouts and toss everything together.

  11. Place in the oven with the squash for 20-25 minutes.
  12. Fill each half of squash with the roasted brussels sprouts and serve.

Recipe Notes

  • Vegetarian Option: Omit the pancetta to make this recipe vegetarian, and vegan.
  • Pancetta substitution: diced thick cut bacon can be used instead of the diced pancetta.
  • Cranberry substitution: dried cranberries can be substituted for fresh cranberries. They should be added to the brussels sprout filling after it's roasted. Frozen cranberries can be used in place of fresh cranberries with no change to the roasting time.