Baked acorn squash with vanilla bean paste, brown sugar, and salt. Such a great small Thanksgiving side dish recipe if you’re making a small Thanksgiving dinner this year, or a Thanksgiving for two.

Roasted Acorn Squash with Vanilla and Brown Sugar

This post is lovingly sponsored by one of my very favorite companies to work with–Nielsen-Massey Vanillas. I was compensated by Nielsen-Massey for my time in developing this recipe and post. As always, all opinions are my own. And I really do love their products.

We made it! We’re at the final side dish for our Thanksgiving for Two gathering! 

All that’s left is pumpkin pie with coconut milk, for which I’m totally making you wait ’til Monday. I think you might be grocery shopping for your Thanksgiving meal this weekend, so I don’t want you to miss an opportunity to pick up ingredients. Go ahead and buy a can of pumpkin and full-fat coconut milk. 

So this baked acorn squash recipe may seem like an afterthought since the dawning of my melting sweet potatoes recipe. But I think when you taste them, you’ll agree they’re both delicious and they deserve equal real estate on your Thanksgiving plate. Even if it’s just a ring or two, you’re going to want to toss them on your plate. Wait, are we playing ring toss with baked acorn squash on Thanksgiving?

Since it’s the holidays, I usually buy some fancy vanilla bean paste. My friends at Nielsen-Massey sent me a bottle of their finest, and when I’m not drinking it with a straw, I slather it on baked acorn squash. And toasted, buttered bread. And I make curly cues with it in my oatmeal. I’ve even been known to drizzle it in a Bourbon cocktail. It just goes with everything.

Baked acorn squash serving size:

The thing I love about this recipe is that it’s easy to scale up or down. I plan on one acorn squash per two people. That’s generally a smidge too much, but it will give you a few leftover rings for the next day. But when you slather an acorn squash in vanilla bean paste, brown sugar, salt, and olive oil, you just may not have any leftovers!

Step-by-step for baked acorn squash:

Vanilla Acorn Squash

Take one beautiful, heavy acorn squash, wash it, and slice it in half.

Roasted acorn squash recipe

Then, slice it into pretty rings, leaving the skin on.

Acorn Squash in the oven

The skin gets meltingly tender in the oven, trust me.

How to roast an acorn squash

Grab your bottle of Nielsen-Massey pure vanilla bean paste, and smooch it before opening.

How to cook acorn squash

Add 2 teaspoons of vanilla bean paste to the bowl, followed by 2 tablespoons of brown sugar, and two big pinches of salt. (This is for one squash, or two servings. Double it, as needed. I’ll paste the recipe below in an amount to serve 4).

Oven roasted squash

Drizzle in 2-3 tablespoons of olive oil, and whisk everything together. Brush all of the squash with the mixture until evenly coated.

Oven roasted acorn squash rings

Do you see the beautiful vanilla bean specks on the squash? Now, roast at 425-degrees for 15 minutes, flip each ring, and roast for another 15 minutes.

Vanilla roasted acorn squash

I also included this baked acorn squash recipe in my Thanksgiving Recipes Sides recipe roundup!

Yield: 4 servings

A Small Thanksgiving: Vanilla Bean Roasted Acorn Squash

A Small Thanksgiving: Vanilla Bean Roasted Acorn Squash

This roasted acorn squash is the perfect side for Thanksgiving.

Prep Time 10 minutes
Cook Time 30 minutes
Total Time 40 minutes


  • 2 acorn squash
  • 4 teaspoons Nielsen-Massey pure vanilla bean paste
  • 4 tablespoons light brown sugar
  • 4 big pinches salt
  • 4-5 tablespoons olive oil


  1. Preheat the oven to 425.
  2. Slice the acorn squash in half, and scoop out the seeds.
  3. Lay the flat part of the squash down on the cutting board, and slice it into rings.
  4. In a medium bowl, whisk together the vanilla bean paste, brown sugar, salt and olive oil.
  5. Brush the vanilla mixture over both sides of the squash rings.
  6. Roast for 15 minutes, flip each ring, and roast for another 15 minutes.
  7. Serve warm.

Nutrition Information:



Serving Size:


Amount Per Serving: Calories: 251Total Fat: 17gSaturated Fat: 2gTrans Fat: 0gUnsaturated Fat: 14gCholesterol: 0mgSodium: 140mgCarbohydrates: 26gFiber: 5gSugar: 11gProtein: 1g

Did you make this recipe?

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