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Home / Fall Favorites

Showstopper Roasted Squash

Roasted squash mashed with butter and brown sugar for a simple and delicious side dish everyone will love.

Erren Hart

|

last Updated:

10/25/2020
5 from 10 votes
Jump to Recipe
Serves: 4
Prep: 15 minutes mins
Cook: 45 minutes mins
Mashed squash with butter in a squash shell

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This Showstopper Roasted Squash recipe brings all the joy of fall to your table. Buttery sweet mash served in its shell to wow your guests.

Serve alongside roasted green beans and honey and maple roasted parsnips for the perfect sides to any holiday meal.

Mashed squash with butter in a squash shell
Pin This Recipe For Later!

Oven roasted squash is really easy to make, and serving it in its shell (with its own handy lid) keeps it warm until you are ready to eat! It’s the perfect side dish for any holiday table or Sunday roast.

Why This Recipe Works

  • Using brown sugar helps bring out the natural sweetness of the squash.
  • Adding Butter gives the mash a creamy consistency as well as a buttery flavor.
  • Serving the squash in its shell helps keep the dish warm before serving and makes a showstopping centerpiece to add to your dinner table.
  • A little salt and pepper cut the sweetness giving a perfect balance.

What Squash Is Best

a variety of different squashes

For this recipe, I used dumpling squash, but you can use any pumpkin or similarly shaped squash that you like to cook with such as Kabocha, Buttercup, or Acorn squash (you may have to trim the bottom to have it stand upright).

As you’ll need to make extra to fill the shells, butternut squash is a great addition to whatever squash you’re filling.

Mashed Butternut Squash

This recipe doesn’t have to be made using the shells. You can make it using cubed butternut squash that you roast and then mash in a bowl with the butter and brown sugar before serving as a side-dish.

How To Make Mashed Roasted Squash

Cut the top off the squash.

A sharp knife slicing the top off a squash

Scoop out the seeds just as you would do when making a Jack-o’-lantern.

a spoon scraping seeds from the inside of a squash

Coat with oil or cooking spray.

a hollowed-out squash sprayed with cooking spray

Place the squash with its lid onto a baking tray and roast for 45 minutes. Once out of the oven add butter and brown sugar.

roasted squash with butter and brown sugar sprinkled on it

Mash the squash into the shell using a fork.

a fork mashing the inside of roasted squash

Leave a border of unmashed flesh to keep the shell stable and to prevent collapsing (about a half-inch will do)

Season with salt and pepper and serve in the shell.

a roasted squash shell with mashed squash filling

Please note – This recipe calls for eight squash, but only serves four shells as it takes two squash to fill one shell (as pictured).  Just remove the flesh from the extra squash, and add it to the one you’re serving before mashing. 

More Roasted Vegetables

  • Best Ever Broccoli
  • Roasted Green Beans
  • Roasted Carrots
  • Roasted Potatoes
  • Garlic Roasted Potatoes

Tips For Best results

  • You can use lids to keep the squash warm for up to 15 minutes. Anything longer will require keeping them in a warm oven.
  • Depending on the size of your squash, cooking times will vary. Check for doneness at around 40 minutes. It’s done cooking when the flesh is tender all the way through to the skin.

FAQs

Do you have to peel squash before roasting?

As this recipe shows, you do not need to peel your squash before roasting. However, you can peel the extra squash, slice into cubes, and roast on an oiled oven tray.

What do you eat with roasted squash?

Roasted squash goes with anything from fish, chicken, pork or beef.

Can you freeze roasted squash?

You can freeze the mashed squash removed from the shell in an airtight, freezer-safe container for up to three months.

How do I store leftovers?

Store (removed from the shell) in an airtight container in the refrigerator for up to days.

Recipe Variations

  • Use maple syrup in place of the brown sugar for a delicious alternative.
  • For a savory twist, leave out the sugar and add your favorite chopped herbs.
  • Add shredded cheese instead of sugar before mashing for an all-new dish the kids will love!

Rate This Recipe

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Recipe

Showstopper Roasted Squash

Roasted squash mashed with butter and brown sugar for a simple and delicious side dish everyone will love.
5 from 10 votes
Print
Prep Time: 15 minutes mins
Cook Time: 45 minutes mins
Total Time: 1 hour hr
Serves 4

Ingredients

  • 8 Squash (Dumpling or similar squash)
  • cooking spray
  • 8 tablespoons butter
  • 4 teaspoons brown sugar
  • salt and pepper to taste

Instructions

  • Preheat the oven to 400F/200C
  • Start by cutting the top off the squash and removing the seeds (just like when you make a jack-o’-lantern).
  • Coat with cooking spray. Place on a baking sheet with the tops and roast for 45 minutes
  • Add the butter and brown sugar directly into the shell.
  • Using a fork, gently remove the flesh from the sides and bottom of the shell. Leaving a border of unmashed flesh to keep the shell stable and to prevent collapsing (about a half-inch will do).
  • Salt & pepper to taste and serve.

Tips

This recipe calls for eight squash, but only serves four shells as it takes two squash to fill one shell (as pictured).  Just remove the flesh from the extra squash, and add it to the one you’re serving before mashing. 
For this recipe, I used dumpling squash, but you can use any pumpkin or similarly shaped squash that you like to cook with such as Kabocha, Buttercup, or Acorn squash (you may have to trim the bottom to have it stand upright).
As you’ll need to make extra to fill the shells, butternut squash is a great addition to whatever squash you’re filling.
You can use lids to keep the squash warm for up to 15 minutes. Anything longer will require keeping them in a warm oven.
Depending on the size of your squash, cooking times will vary. Check for doneness at around 40 minutes. It’s done cooking when the flesh is tender all the way through to the skin.
Show Nutrition Hide Nutrition

Nutrition

Calories: 553 | Carbohydrates: 91g | Protein: 7g | Fat: 23g | Saturated Fat: 14g | Cholesterol: 60mg | Sodium: 231mg | Potassium: 2640mg | Fiber: 15g | Sugar: 20g | Vitamin A: 80425IU | Vitamin C: 157.5mg | Calcium: 370mg | Iron: 5.3mg
Created by Erren Hart
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Update Notes: This post was originally published in 2014, but was republished with new photos, step by step instructions, cooking tips, and a variations in October of 2020.

5 from 10 votes (5 ratings without comment)

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16 responses

  1. R. Zoerman Avatar
    R. Zoerman
    10/05/2023

    any tips on easy ways of cutting the top off

    Reply
    1. Erren's Kitchen Avatar
      Erren’s Kitchen
      10/06/2023

      Great question! Cutting the top off the squash can be a bit tricky. Make sure the knife you are using is sharp. Before cutting, you can try scoring around it first. If you encounter resistance while cutting, don’t force it. Instead, use a gentle sawing motion to work your way through. I hope these help! Please let us know if you have any other questions! 😊

      Reply
  2. Toni Avatar
    Toni
    09/19/2022

    Do the lids sit on the squash? I just bought a dumpling squash today
    Thanks

    Reply
    1. Erren Hart Avatar
      Erren Hart
      09/20/2022

      Hi Tony, the lids may shrink with roasting so they may not sit well after cooking.

      Reply
  3. Sammy Avatar
    Sammy
    12/06/2021

    I made this at the weekend, so delicious, never would have thought to add the brown sugar!

    Reply
    1. Erren's Kitchen Avatar
      Erren’s Kitchen
      12/06/2021

      It’s a great special ingredient, isn’t it? Glad you liked it 🙂

      Reply
  4. Ian Avatar
    Ian
    10/05/2020

    Wow, just wow, never knew squash could be so tasty 😋

    Reply
    1. Erren's Kitchen Avatar
      Erren’s Kitchen
      10/06/2020

      I’m glad you enjoyed it Ian 🙂

      Reply
  5. karenmaginnis Avatar
    karenmaginnis
    11/15/2014

    One of the best presentation ideas I’ve seen – brava! Simple and delicious, how could we resist?

    Reply
    1. Erren Avatar
      Erren
      11/19/2014

      Thanks so much Karen! 🙂

      Reply
  6. Thalia @ butter and brioche Avatar
    Thalia @ butter and brioche
    11/15/2014

    Love the idea of stuffing squash like this! Definitely a recipe I need to try.

    Reply
    1. Erren Avatar
      Erren
      11/19/2014

      Thanks so much, Thalia! 🙂 Let me know if you try it!

      Reply
  7. Ally Avatar
    Ally
    11/14/2014

    You have to love that a pumpkin comes with it’s own built-in serving dish, and using it to hold it’s own pumpkin mash is ingenious 🙂 So simple and delicious, thank you for sharing!

    Reply
    1. Erren Avatar
      Erren
      11/19/2014

      Thanks, Ally! So glad you like it! 🙂

      Reply
  8. Marie @http://citronlimette.com/ Avatar
    Marie @http://citronlimette.com/
    11/12/2014

    What a nice side dish! Perfect for Thanksgiving!

    Reply
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