Paleo Picadillo Casserole + How to Peel and Roast Butternut Squash

by Leanne Vogel (Healthful Pursuit) on December 5, 2011

No food is more amazing than roasted butternut squash.

And no chocolate cake will change my mind on this.

If roasted correctly, the chunks get these amazing caramelized bottoms.

I can’t promise I didn’t peel off some of them before mashing the squash for the recipe I’m about to share with you.

There are worse things.

The creation of this recipe began as many do – in my kitchen. You see, at the first weekend of every month, I cook 3 shepherd’s pies for Kevin.

It’s the only dinner he likes will eat. It keeps things easy, and I can pretty much make a shepherd’s pie with my eyes closed at this point.

Problem is? I don’t like shepherd’s pie. The gravy, the potatoes… maybe it’s because I’ve made it so many times that I’m just completely turned off? Either way, as I was going on my third batch of garlic mashed potatoes, I had an epiphany.

A butternut squash, raisin, bison, epiphany.

I’ve recently learned that these are the best kind.


Paleo Picadillo Casserole

Gluten free, Dairy free, Sugar free, Yeast free, Corn free, Grain free

The picadillo casserole is a classic Cuban beef hash recipe. Generally it’s made with bacon, ham, cumin, and oregano. But like all things, I had to switch it up a little.

Yield: 1 ginormous casserole

Servings: 10


The meaty parts

  • 1 lb extra lean ground bison
  • 1 lb extra lean ground elk *see note
  • 1 cup white mushrooms, chopped
  • 1 red onion, chopped – yield ~ 1 1/2 cup
  • 3 cloves garlic, minced
  • 2 tsp chili powder *see note
  • 1 tsp ground cumin
  • 1 tsp dried oregano
  • 1/4 tsp Herbamare or Himalayan rock salt

The sauce

  • 28oz. can diced tomatoes (with juice)
  • 3/4 cup kalmata olives *see note
  • 1/4 cup dried apricots, chopped
  • 1/4 cup whole raisins

The topping

  • 2 butternut squash, peeled and chopped into rough cubes – yield ~8 cups
  • 2 tbsp coconut oil, melted
  • 3 tbsp almond flour
  • 1 egg, beaten
  • 1/4 tsp oregano
  • 1/4 tsp Herbamare or Himalayan rock salt


  1. Preheat oven to 400F and line a baking sheet with parchment paper or silicon baking mat.
  2. Cube the squash with the directions below. Then coat with melted coconut oil, lay out on the prepared sheet and roast for 35-40 minutes, until soft.
  3. Meanwhile, place bison and olive oil in a large frying pan. Scramble-fry for 10 minutes or so until no longer pink. Transfer to a paper towel lined plate.
  4. Place mushrooms, onions, garlic, chili powder, cumin, and oregano in the frying pan and cook until the onions have softened.
  5. Add tomatoes, olives, apricots, and raisins. Stir and bring to a boil before adding cooked ground meat.
  6. Spread mixture into a greased 3 quart (3L) shallow baking dish and set aside.
  7. Reset the oven to 375F and mash the squash with a hand masher or blender while mixing in almond flour, egg, oregano, and herbamare.
  8. Spread on top of beef mixture. Place a decorative pattern on top with a fork and bake in 375 oven for 40 minutes.

note: you can use a combination of other meats like beef or all bison if you’d like.

note 2: don’t be scared of adding this much chili powder. I’m not a fan of spicy food and didn’t find it spicy at all. It just adds the perfect amount of flavor!

note 3: olives are technically not paleo because of high salt content. Feel free to replace with red or yellow bell peppers.

View nutrition info (now with nutrition labels!)


How to Peel and Roast Butternut Squash

Have I said how good roasted butternut squash is?

Oh yes, I think we’ve covered that already.

To make your very own at home; because I have a hard time sharing mine – use these simple steps!

Start off with a big bowl, measuring cup, sharp knife and a veggie peeler.

And your squashes. Can’t forget those!

Begin by removing the skins with your handy dandy peeler.

There will be green vains under the skins. Make sure those are removed as well.

Tada! Okay, now do it once more with the other squash.

Now cut the end and top off.

And slice it down the middle (horizontally).

Remove all the guts with a spoon.

Or, if you’re lazy like me and you don’t want to go the 6 feet to the kitchen to get a spoon, hack at it with your big knife and get squash guts all over your living room.


Dice the peeled and gutless squash and place in a bowl with all the ingredients. Stir it around for good measure.

Lay out onto a lined baking sheet.

Having done this a couple times now, I like the results that parchment paper gives more than my silpat. More caramelization is a win in my book!

Roast for 40′ish minutes in a 400F oven then burn the roof of your mouth in a billion spots as you test the best pieces.

Do everything else the recipe above says to do; or just eat the roasted squash from the pan with a spoon, and you have yourself a delicious, filling meal!

I generally don’t like to serve casseroles when we have guests over, but this one is a real winner with it’s amazing sweet and savory tones, popping colors, and amazing presentation.

Someone come over for dinner so I can make this again! Can’t promise your portion will have any mashed squash on it though ;)

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{ 35 comments… read them below or add one }

J3nn (Jenn's Menu and Lifestyle Blog)

You make it seem easy to peel butternut, so I’m going to try it instead of buying the pre-peeled that are only good for about 8 hours after you bring it home. :)



Mmm…I luv butternut squash! I’m going to try this method of peeling..thanks!


Rebecca @ Naturally Healthy and Gorgeous

I love butternut squash but I do hate cutting them. I have to resist being lazy and buying the already cut up ones! :)


Angela @ Eat Spin Run Repeat

I’ll come! I’ll even bring my own squash too, because I have a feeling that no amount would ever be enough for the 2 of us!


Averie @ Love Veggies and Yoga

Thanks for the step by step…I normally feel like I may lose a finger when I cut into b-nut squash….those buggers are so big and tough! :)


Alex@Spoonful of Sugar Free

I have just started roasting butternut squash about a month ago and I use the exact same method as you…I was going to right a post about it, too, but you beat me to it! Haha…Love the recipe :D


Miranda @ Living One Bite at a Time

Wow this recipe looks great! I LOVE butternut squash, too. Also, glad to know I’ve actually been doing the whole “prepping a butternut squash” thing right haha!



I absolutely love roasted butternut squash!! That recipe looks divine, my husband is a meat eater so he would appreciate me making this!! Although I have no idea where to buy bison or elk?


Leanne (Healthful Pursuit)

I purchase our wild game at the local butcher. If you don’t have anything like that around, you can go for grass-fed beef as well!



1 ginormous casserole is going into my oven this evening



Leanne (Healthful Pursuit)

Very nice! Haha it really makes a lot. I’ll be eating this thing for awhile. Enjoy!



this is a very timely post for me, I have a Butternut squash that I need to use today and I had no idea how to peel it. Thanks so much. I think I will just eat the roasted squash but I will definitely have to try this recipe once our deer meat is finished being processed.


Leanne (Healthful Pursuit)

Deer meat would be awesome with this! You’ll have to let me know how it goes :)


katie @KatieDid

Looks SO up my alley. I usually top a sweet potato with warmed up chili for a quick meal which is similar to this.


Leanne (Healthful Pursuit)

I love the idea of using chili as a topper to sweet potato! I’ll have to give that a try :)



mmm i love butternut squash! but im too lazy to peel it….i cut and roast it with the skin and eat it afterwards! still just as good to me!


Carolyn @

Yum! I’ll come over! ;)


Sarena (The Non-Dairy Queen)

I love roasted butternut squash! It gets all sweet and caramel and warm and yummy!



I am LOVING butternut squash lately! Mmmmm mmmm! :)

On an unrelated note, I made your recipe for glazed apples this morning and loved how they turned out. The use of tapioca is brilliant, I would have never thought of that! Where do you come up with these things?! :)


Leanne (Healthful Pursuit)

I’m so happy you liked the apples! Honestly? For that recipe… I was thinking: wouldn’t it be cool to have pie filling on pancakes? But pie filling can be That’s a pretty long a drawn out process, so I tried to improvise. A lot of it just comes as I go!


Jenn @ Peas and Crayons


ahhh i love it! and roasting squash is a pain in my tush but OH SO worth it! I need to buy more!!!



Yum that really looks delicious and is definitely going on my menu within the next couple of days. Thanks for sharing :)



I’m making the crock pot variation with pan fried variation of the butternut squash (temporary living arrangement ~ no oven). I must say…I’ve never had butternut squash before and I have a slight contempt for regular potatoes now!

Great dish! It’s going on my “Cook to Kill” list for potential guests…:-)


Leanne (Healthful Pursuit)

I wish I would have made this in my crockpot! How brilliant! Totally doing that next time, thanks for the idea, and I’m glad you like it!


Kelli W

We love butternut squash! Your recipe picture looks like you’ve used some seasonings on your squash? Can you tell me what they are?


Leanne (Healthful Pursuit)

Hi Kelli – it’s oregano that I added to the squash after cooking. In the recipe it calls for it afterward as I felt it would give better flavor that way. Enjoy!



Can this be made ahead and frozen?


Leanne (Healthful Pursuit)

You bet it can! I made the whole batch, had a bowl then froze it all in single serving containers. Worked out great!


GiGi Eats Celebrities

THIS is being bookmarked. DONE!
Oh and question for you: I peel and bake butternut squash like a hooker spends time on a street corner… yeah, that’s not my question… or even a question, but I was curious… if you don’t wear gloves, do your hands get REALLY dry from touching the butternut squash??? Or is this just me and I have some sort of weird allergic issue with it??


Leanne (Healthful Pursuit)

Hi Gigi – no, my hands don’t get dry at all! That’s so odd!



I made this for dinner tonight. My husband loved it! He said it was in his top 5 favorite meals ever eaten. Thank you!



Thank you! I’ll need to make a lot of substitutions to make this AIP friendly, but I like the basic idea. I like to cut my squash in half before peeling.



This looks sooo yummy. We love to use bison. I have a little hint I learned from Martha.. Use your mellon-baller to scrape the seed compartment of any squash or an apple or pear. The sharp edge of this little tool cuts right through the crisp flesh and leaves the ramaining cavity clean.


Leanne Vogel (Healthful Pursuit)

That’s SUCH a great tip. Thanks Mindy ;)



This is in the oven right now and smells so good.
I had to improvise with what I had.
Ground turkey and beef for the meat. No olives or apricots so I just omitted them!
I’m sure it will taste yummy though. Thanks.


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