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Oct 30 2015

Roasted Maple Brown Sugar Cinnamon Acorn Squash

Find the recipe card at the end of the post. Make sure to read the content as it contains chef tips, substitution options, and answers to FAQs to help you succeed the first time around!

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Oh Fall how I love you…sorta. The change in the leaves are gorgeous, sure…until you have to rake 5 acres worth. The weather is cooler…and rainy/gray if you live in Pittsburgh. You start off the morning wearing a jacket to work…only to have to carry it on the way home as it’s hot. But there are somethings that one cannot argue with about the awesomeness of Fall…

♥ Steelers Football
♥ Pittsburgh Penguins Hockey
♥ Halloween
♥ Halloween Candy
♥ Dress boots (I’m such a girl when it comes to boots)
♥ and lastly, Winter Squash

If you recall from one of my earlier posts I shared with you how to pick the perfect winter squash. Following my own advice I picked up a bunch of squash at the market – acorn, butternut, spaghetti just to name a few.  See one thing I LOVE about these squashes is that since their flavors are so mild, they truly are such a versatile ingredient to work with.  They are great in desserts as well as savory dishes.  Today I have a combination of both – sweet and savory for you.  I see this dish as a perfect Thanksgiving dinner side dish or for those nights when you just want to go vegetarian.

Maple Brown Sugar Acorn Squash3

This dish couldn’t be any easier to prepare to be honest.  I think the hardest part is literally cutting it in half.  That’s where you need to use your muscles or call on some sexy beast to help you.  “Oh Mr. Fantabulous dear…”  LOL  Actually I was able to cut this myself.  The easiest way I found was to insert the tip of a very sharp knife into the squash, go in about half way and then start to slice downwards rotating the squash as I did.  When I got to the stem I just went to one side of it as there is no way in the world I could have sliced that thing in half.

With the squash in half I scooped out the seeds and discarded them.  However did you know you can roast them just like pumpkin seeds?  Yep!  They are pretty tasty too!  However I was short on time so I pitched them. Rolling the squash over I cut it across into 1″ thick slices.  You could make them thinner but I wanted something with substance.  Keep in mind if you do cut them thinner you’ll definitely need to reduce the cooking time.

Maple Brown Sugar Acorn Squash

As I said earlier, with squash you can go a million ways from Sunday in how you season these.  Since I was serving a cinnamon spiced pork loin as the main course I wanted flavors that would marry well with it.  Maple syrup (the real stuff, not the fake… ever), light brown sugar, cinnamon and some salt is all this really needed.  Now if you wanted to elevate this just a bit more you can add about a 1/4 teaspoon of chili powder to the mix.  Yes, chili powder.  The heat is barely noticeable but what is noticeable is the depth of flavor it gives.

Maple Brown Sugar Acorn Squash1

As these wedges roasted my kitchen was full of warm spices.  Seriously I LOVE the smells of Fall flavors in my kitchen.  It’s just so warm and comforting.  What is awesome is when maple syrup combined with brown sugar and butter bakes, it becomes thick and almost caramelized.  It sticks to the squash and coats every single bite of it.  When it came out, I plated it and then for kicks, drizzled just a teaspoon more of maple syrup on top.  Why not, right?!  As you can see the wedges come out positively glistening and coated in strands of the brown sugar and cinnamon. One thing I will warn you about it sugar, when hot burns…like alot! So watch your fingers.

I actually let this set for about 5 minutes before we ate just so neither of us burned our mouths.  Well okay *I* would have known well enough not to stuff it into my mouth without feeling it first however my human vacuum sweeper would have just inhaled first then gasp that it was too hot or he burnt his mouth.  LOL

Maple Brown Sugar Acorn Squash2

Now we both loved this recipe however Mr. Fantabulous was not too keen on the fact that the rinds were still on.  They have to be while you bake them and yes, they are perfectly edible once baked.  The rinds are so thing, that when baked, they are about the same texture of a baked apple peel.  He, had issues with this as it “wasn’t how his mother made them.” Oy!  He wanted no parts of eating the rind and even gave me the ‘grossed out’ eye when I just ate them whole.  Kids, I swear!  So it’s your choice to eat the rind or not either way, you’re definitely going to LOVE this dish!

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Roasted Maple Brown Sugar Cinnamon Acorn Squash

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5 from 3 reviews

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  • Author: The Kitchen Whisperer

Ingredients

  • 1 large acorn squash, sliced in half and seeded
  • 2 tablespoon melted butter, unsalted
  • 2 tablespoon light brown sugar
  • 1/2 teaspoon cinnamon
  • 2 tablespoon maple syrup plus additional for drizzle
  • 1/4 teaspoon salt

Instructions

  1. Preheat the oven to 400F, rack in the middle.
  2. Line a rimmed baking sheet with foil.
  3. Spray the foil with baking spray.
  4. Slice each acorn half in 1” thick wedges.
  5. Place the wedges into a large mixing bowl.
  6. To the bowl add the rest of the ingredients.
  7. Gently mix/toss to coat all sides of the acorn wedges.
  8. Using tongs place each wedge onto the foil. Do not overlap.
  9. Bake for 30-35 minutes or until the squash is fork tender but not mushy.
  10. Remove from the oven and plate.
  11. Drizzle with additional maple syrup if desired.

Notes

If you want to elevate this a bit, add in a 1/4 teaspoon of chili powder to the mix.

Also when it only has about 10 minutes left to bake, toss on some chopped pecans to give it some texture.

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5 responses

  1. Lidia
    October 18, 2025

    I love acorn squash when cooked more like a dessert and this recipe hits just right! So much easier to serve this way and delicious for kids too !
    The pecans added at the end totally worth it!
    Thank you Chef!

    Reply
    1. Lori
      October 19, 2025

      So happy you loved this Lidia! Agreed, I’m all about the pecans with this as well!

      Best Kitchen Wishes!

      Reply
  2. Diane
    January 26, 2021

    My family loved this!

    Reply
  3. Lisa
    May 2, 2020

    I was looking for something to go with pork tenderloin and this was it! I’m not a huge vegetable eater, so any way I can find to incorporate more into my meals is a win. This was very good and I followed the recipe as is – everyone liked it!

    Reply
    1. TKWAdmin
      May 5, 2020

      Thank you so much Lisa! So happy everyone loved the recipe!

      Best Kitchen Wishes!

      Reply

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I’m Lori, The Kitchen Whisperer®! Let me help you tame the kitchen one bite at a time.

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