This twice-baked acorn squash is filled with Tuscan kale, hearty freekah and Pecorino Romano for a cozy fall side with a subtle protein boost.
*This post is sponsored by Vital Proteins
When my parents recently downsized after 26 years in one house, I ended up with two boxes of family things — photos, school papers, diplomas and some unexpected heirlooms. Sifting through childhood photos and every progress report confirmed my lifelong nerdiness, but the one item I couldn’t part with was a small blue box of genuine ivory flatware from my dad’s family in India.
My dad’s family history is sparse: he was raised in an unusual household and brought very few possessions with him when he moved to the United States at 18. Those ivory utensils, clearly well-lived-in and decades old, felt like a tangible piece of family memory worth keeping. That quiet comfort is what inspired this recipe as much as the utensils themselves — a dish meant to feel warm, familiar and satisfying.
This twice-baked acorn squash combines nutty freekah (a roasted green wheat that deserves more attention), thinly sliced Tuscan kale, savory Pecorino Romano and fragrant rosemary. The filling is hearty enough to stand on its own as a main for lighter meals, or it makes an excellent side for a larger fall spread.
You can swap the freekah for other hearty grains you have on hand — barley, farro, brown rice or wheatberries all work well — and the filling adapts easily to other squash varieties like sweet dumpling, delicata or red kuri.
For an added nutrition boost, this version includes Vital Proteins collagen peptides. The powder is flavorless, dissolves easily and increases the protein content while contributing potential benefits for joint, bone and gut health. I often add collagen peptides to baked goods, soups and even my morning coffee — they add nutrition without changing taste or texture.
Comfort food, especially in autumn, is about more than flavor — it’s about the feeling it invokes. This stuffed squash is cheesy, savory and wholesome, with textures and flavors that feel both rustic and thoughtful.
Looking for other acorn squash ideas? Try baked white acorn squash with maple or coconut-crusted acorn squash rings for different sweet and savory takes.
Love this Twice Baked Acorn Squash recipe?
Try other fall-inspired recipes such as Creamy Almond Butter Fall Pasta, Creamy Coconut Delicata Squash Soup or Roasted Sweet Potato, Squash and Chickpea Fall Salad with Maple Tahini Dressing.
Twice Baked Kale and Pecorino Acorn Squash
Ingredients
- 2 small acorn squash
- 2 tablespoons extra virgin olive oil
- 1/3 cup freekah, or another hearty grain such as barley, farro or brown rice
- 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 lacinato (Tuscan) kale, thinly sliced
- salt and pepper
- 2 scoops, 20 g Vital Proteins collagen peptides
- 1/2 cup grated Pecorino Romano cheese, plus more for topping
Instructions
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Preheat the oven to 400°F (200°C).
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Cut each acorn squash in half and scoop out the seeds. Brush the cut sides with olive oil and place the squash cut-side down on a greased baking sheet.
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Roast for about 20 minutes, until the flesh is tender but the squash still holds its shape.
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Meanwhile, combine freekah and broth in a medium saucepan. Bring to a boil, then reduce heat, cover and simmer until the liquid is absorbed. Set aside.
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Melt the butter in a large skillet over medium heat.
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Add the sliced onion and minced rosemary and sauté until softened, about 5 minutes.
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Add the kale and cook another 3–5 minutes until wilted. Season with salt and pepper to taste.
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Transfer the kale mixture to a large bowl and combine with the cooked freekah, collagen peptides and grated Pecorino Romano.
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Scoop a portion of the roasted squash flesh into the bowl, leaving enough in each shell so the halves remain sturdy.
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Mix the filling thoroughly, then spoon it back into each squash half.
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Top with additional Pecorino Romano and return to the oven for 10 minutes to heat through and melt the cheese. For a golden, crispy top, finish under the broiler for 1–2 minutes—watch closely.
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.