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Twice Baked Kale and Pecorino Acorn Squash

This twice baked acorn squash is stuffed with tuscan kale, hearty freekah and pecorino romano for a lovely fall side with a hidden protein boost.

*This post is sponsored by Vital Proteins
This twice baked acorn squash is stuffed with tuscan kale, hearty freekah and pecorino romano for a lovely fall side with a hidden protein boost.

In my parents’ move last month from their house of 26 years to one half the size, I ended up with 2 boxes of everything from pictures to every single school letter, test, diploma, award you can imagine to random ivory utensils from my dad’s family in India.

While baby pictures of myself all the way through high school graduation (thanks for those excellent bangs circa 3rd grade, mom) definitely provided some entertainment just as looking back on every single progress report and report card from grades K-12 re-affirmed my legit nerd status (that got me nowhere in life, glad I wasted all those hours studying).

As I sorted my way through the boxes, the one actual item that didn’t make its way into a garbage bag was this blue box filled with these real ivory flatware.

Freekah gives these twice baked acorn squash a hearty, fall feel.
Tuscan kale and freekah combine for a hearty take on twice baked acorn squash.

We know so little about my dad’s side of the family. He’s an only child from a split household (a really long and bizarre story on that) who grew up in India but isn’t of Indian descent at all.

He was raised orthodox Jewish (with an Italian catholic mother) but from somewhere in the middle east (Iraq?).

He moved to the states at 18 and the amount of family memories/heirlooms that made their way over could probably fit in a small box at most.

It’s equal parts sad and intriguing.

Give your side dish a hidden protein boost with collagen peptides. They're tasteless but add a nice healthy kick to these twice baked acorn squash.
Kale, freekah and pecorino romano combine in these fall inspired twice baked acorn squash.

Needless to say, these ivory utensils that date back at least to his childhood are something I’ll gladly keep (unlike the pictures of my braced, 5th grade, ‘blew up like a tick before growing 6 inches’ self) from the box of memories my mother gave me.

I wouldn’t say the utensils inspired this recipe for twice baked acorn squash as much as created a sense of comfort within making me want to translate that feeling to food.

Stuffed with hearty freekah (a lovely grain that doesn’t get as much attention as it deserves), kale, pecorino romano and aromatic rosemary, the comforting, cozy factor definitely comes through in these twice baked acorn squash.

This twice baked spaghetti squash recipe would’ve done the trick too for some coziness if that’s the type of squash you have on hand.

You can also use this filling in other squash. Sweet dumpling squash and stuffed delicata squash are both great options. And red kuri squash is a newer to me winter squash find that’s also great roasted and stuffed.

These twice baked acorn squash are a lovely, hearty fall dish that's plenty filling on its own or perfect as a side.
Twice baked acorn squash makes a great side dish for any fall meal.

It’s also boosted with health supporting Vital Proteins collagen peptides, a tasteless addition that not only adds extra protein but an array of bone, joint and gut benefits as well.

I’ve added it to butternut squash biscuits, nectarine upside down cakemango melon soup in the past as well as my mug of morning coffee every single day and you’d never know.

It detracts nothing from the food while giving you all those added health benefits, a complete a win win.

Cheesy, hearty and packed with healthy superfoods and protein, these twice baked acorn squash are a must for your fall dinner table!

Comfort food is the best kind of food, isn’t it?

Looking for other acorn squash recipes? Try this easy maple baked white acorn squash side dish or these fun coconut crusted acorn squash rings!

Love this Twice Baked Acorn Squash recipe?

Try these other fall inspired recipes: Creamy Almond Butter Fall PastaCreamy Coconut Delicata Squash Soup and Roasted Sweet Potato, Squash and Chickpea Fall Salad with Maple Tahini Dressing.

Twice Baked Kale and Pecorino Acorn Squash

This twice baked acorn squash is stuffed with tuscan kale, hearty freekah and pecorino romano for a lovely fall side with a hidden protein boost.
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Prep Time 15 minutes
Cook Time 35 minutes
Total Time 50 minutes
Servings 4 servings


  • 2 small acorn squash
  • 2 tablespoons extra virgin olive oil
  • 1/3 cup freekah or other hearty grain like barley, brown rice, farro, wheatberries, etc.
  • 3/4 cup broth chicken or vegetable
  • 1/2 tablespoon butter
  • 1/2 large red onion thinly sliced
  • 1 tablespoon minced rosemary
  • 1 small bunch lacinto kale thinly sliced
  • salt and pepper
  • 2 scoops 20g Vital Proteins collagen peptides
  • 1/2 cup grated pecorino romano cheese plus more for topping


  • Preheat oven to 400 degrees.
  • Cut acorn squash in half to create two bowls out of each. Scoop out the seeds, drizzle with the olive oil and place cut side down on a greased baking sheet.
  • Roast for about 20 minutes until flesh is softened but the squash is still firm enough to hold it’s shape well.
  • While squash roasts, combine freekah and broth in a medium sauce pot over high heat. Bring to a boil, stir, reduce to low, cover and cook until all the liquid is absorbed by the freekah. Set aside.
  • Place the butter in a large skillet over medium heat.
  • Add the onion and rosemary and saute until softened, about 5 minutes.
  • Add the kale and cook another 3-5 minutes until wilted. Season to taste with salt and pepper.
  • Place the kale mixture in a large bowl with the cooked freekah, collagen peptides and cheese.
  • Gently scoop out some of the flesh of the acorn squash, leaving enough in the squash so that it stands up and holds its shape well and place it in the bowl.
  • Mix the ingredients in the bowl together and scoop them back into each squash half.
  • Top with additional pecorino romano and return to the oven for another 10 minutes to warm through and melt the cheese. Finish under the broiler for about 2 minutes for a golden brown and crispy top.

Nutrition Facts

Serving: 1SERVING | Calories: 266kcal | Carbohydrates: 22g | Protein: 20g | Fat: 12g | Saturated Fat: 4g | Polyunsaturated Fat: 8g | Cholesterol: 18mg | Sodium: 334mg | Fiber: 6g | Sugar: 2g

This website provides approximate nutrition information for convenience and as a courtesy only. Nutrition information can vary for a variety of reasons. For the most precise nutritional data use your preferred nutrition calculator based on the actual ingredients you used in the recipe.

Cuisine American
Course Side Dishes
Keyword baked acorn squash, kale and pecorino acorn squash, twice baked acorn squash

Gina Matsoukas is the writer, founder, photographer and recipe developer of Running to the Kitchen — a food website focused on providing healthy, wholesome recipes using fresh and seasonal ingredients as much as possible. Her work has been featured in numerous media outlets both digital and print, including MSN, Huffington post, Buzzfeed, Women’s Health and Food Network.

Recipe Rating


Saturday 19th of November 2016

This looks so perfect! I love stuffing acorn squash!

Cookin Canuck

Friday 18th of November 2016

What an interesting background your dad has! What an awesome idea to slip the Vital Proteins into this squash for an extra boost of nutrition. And I love anything that involves freekah.

Rachel @ Rachel Cooks

Friday 18th of November 2016

I need to make this for lunch today!

Wendy | Around My Family Table

Thursday 17th of November 2016

WOW! This looks amazing. It would be great on our holiday table next week.

Bethany @ Athletic Avocado

Wednesday 16th of November 2016

Comfort food for sure is the best kind of food! Love me some stuffed squash with sweet and savory flavors! Such a great idea to add collagen for a flavorless protein boost!