Skip to Content

Apple Cranberry Stuffed Acorn Squash

This acorn squash recipe from Catherine over at Whine and Dancing has solved so many of my Thanksgiving problems. From making sure we’re including enough veggies, to cooking dishes that don’t take hours and hours to prepare, this Apple Cranberry Stuffed Acorn Squash recipe is the perfect compliment to a Thanksgiving meal. 

The best part is, even if you’re not a fan of acorn squash, you can still make the amazing apple cranberry relish as a delicious alternative to the traditional gelatinous canned cranberry that comes out with can lines in it (my apologies to anyone who actually eats that stuff!) The relish would be delicious on turkey, or stuffing, or…on a fork. Just sayin’. 

If you’re looking for other Thanksgiving recipes, don’t forget to check out my Paleo Thanksgiving Roundup, which will get you all the way from appetizers to desserts without gluten, dairy, soy, and post-meal tummy aches. 


Hi everyone! My name is Catherine from Whine and Dancing. Jessica has kindly agreed to let me share one of my new recipes with you: Apple Cranberry Stuffed Acorn Squash.

I have to confess that my blog is not specifically a Paleo blog, nor does my family eat Paleo. In fact, my family of picky eaters has a really difficult time with most vegetables. For years, my biggest struggle was getting my husband to eat more than just corn and green beans. You can read more about my crazy, picky family on my blog.

Since I am always working on getting my picky eaters to eat more adventurously, I was pleasantly surprised when they enjoyed this new acorn squash recipe.

To prepare the acorn squash, I cut it in half lengthwise and scooped out all the seeds to make a nice bowl that could be loaded up with that delicious sauce. I also sliced off a little bit of the squash on the bottom of the “bowl” so that they would sit flat on the sheet pan. Roasting any squash in the oven with salt and oil is my favorite way to prepare it.

While the acorn squash is roasting until the flesh is nice and soft, I prepare the sauce on the stovetop (be careful, because those fresh cranberries will start popping as they cook down).

The simple, flavorful apple cranberry sauce would be a great Thanksgiving dish all by itself, but I decided put it inside these golden roasted acorn squash bowls.

When that sauce was simmering on the stove, it certainly made me want to start playing holiday music and decorating for winter. My husband even asked me what flavor candle I was burning!

After the sauce is finished, I turned it off to cool down a bit. As the sauce cools, it will thicken up even more. Once the acorn squash is nice and golden, remove from the oven and top with the sauce. I added some orange zest as well to brighten and enhance the flavors.

Enjoy! This acorn squash recipe makes a great side dish that pairs nicely with my Slow Cooker Apple Cider Pork Loin  (substitute honey for the brown sugar to make it more Paleo friendly).

Apple Cranberry Stuffed Acorn Squash

Apple Cranberry Stuffed Acorn Squash

Yield: 6 people
Prep Time: 10 minutes
Cook Time: 45 minutes
Total Time: 55 minutes

Acorn squash gets a sweet and tart filling; the perfect fall side dish!



  • 3 acorn squash, , halved and seeded
  • 2 Tablespoons olive oil
  • 1 teaspoon salt

Apple Cranberry Sauce:

  • 2 cups fresh cranberries
  • 1 large Granny Smith apple, cored and diced
  • 2 oranges
  • 1/2 cup water
  • 1/2 cup honey
  • 1/2 teaspoon ground cinnamon
  • 1/4 teaspoon ground ginger
  • 1/4 teaspoon ground allspice
  • pinch of salt
  • orange zest, for garnish


  1. Preheat oven to 400°.
  2. On a prepared sheet pan, place 6 halves of acorn squash. Cut off the bottom of the "bowl" if needed so the squash will sit flat. 
  3. Use a brush to coat the acorn squash bowls with olive oil, then sprinkle with salt.
  4. Place the pan in the preheated oven and roast the squash for 30-40 minutes or until tender. 
  5. While squash is roasting, in a large saucepan combine all remaining ingredients for the apple cranberry sauce except for the orange zest. 
  6. Bring to a boil, then reduce heat and simmer for 15 minutes. Turn heat off and allow to cool until sauce thickens.
  7. Remove squash from oven. Fill each acorn squash bowl with apple cranberry sauce, dividing evenly.
  8. Garnish with orange zest and serve!
Nutrition Information:
Yield: 6 Serving Size: 1
Amount Per Serving: Calories: 244Total Fat: 5gSaturated Fat: 1gTrans Fat: 0gUnsaturated Fat: 4gCholesterol: 0mgSodium: 382mgCarbohydrates: 53gFiber: 8gSugar: 32gProtein: 2g

I’m Catherine,  a wife to a wonderful husband and mom to three smart kids! I am also a baker, cook, maid, writer, blogger and photographer. I am a small town Texan with a love for chocolate, wine and reading! I love to try new recipes and modify them for my crazy picky family. My goal is to help busy families with simple, delicious recipes. At Whine and Dancing, we are dancing in the kitchen and tuning out the whine to get dinner on the table!

Follow me on Facebook, Twitter, Pinterest, and Instagram!

Get Access To My Free Resource Library!
Includes tips for clean eating, a Paleo staples checklist, bodyweight workouts, and more – all with a side of awesome sauce!

This form collects information we will use to send you updates about promotions, special offers, and news. We will not share or sell your personal information. You can unsubscribe at any time.


3 Steps to Meal Planning |
How To Meal Plan In Just 30 Minutes a Week
← Read Last Post
25 Perfect Paleo Pumpkin Recipes
Read Next Post →

Skip to Recipe