Gather and prepare all ingredients. Peel the butternut squash, cut off the ends, and cut the squash in half where the narrow neck meets the bulbous base. Slice the bulbous base in half lengthwise, scoop out the seeds, then cut both the neck and the seeded portion into small-sized cubes.
Heat the vegetable oil in a large skillet or Dutch oven over medium heat. Once hot, add the cubed butternut squash in an even layer. Cook for about 15 minutes, stirring every 5 minutes, until the squash is tender and nicely browned on several sides.
After 15 minutes, add the diced onions, garlic, ½ teaspoon of salt, and ½ teaspoon of pepper. Sauté for about 3 minutes until the onions are softened.
Add the orzo pasta, vegetable broth, and remaining salt and pepper. Stir to combine.
Bring the pot to a boil, then reduce to a medium simmer. Cook for 10 minutes, stirring constantly to help break down the squash and orzo. This will help make it thick and creamy.
After 10 minutes, add the cinnamon, chopped kale, and heavy cream. Stir until the kale has wilted, about 2-3 minutes.
Divide the butternut squash orzo into bowls, sprinkle on the fresh Parmesan, and enjoy.
*Look for a butternut squash that feels firm and heavy for its size, with matte tan skin and no soft spots. Brown it for the full 15 minutes so it has time to soften properly. Pre-cut squash works too, but chop larger pieces smaller. For frozen squash, I’d thaw and pat it dry first, since extra moisture can make it steam instead of brown.**I use orzo pasta because I want it to break down and become thick and creamy, and it’s SO easy to use in a one-pot meal! You can also use other pasta like penne, rigatoni, farfalle (bowtie), or fusilli. Be sure to read the cooking instructions and adjust the broth amount as needed. The result will not be as thick and creamy as the orzo, but it will still be delicious.***I like to use Better Than Bouillon to make broths to keep costs low.****I love kale and think it’s a great addition to this recipe. It’s fresh and peaks in the fall, so I love adding it to this pasta. Remove the tough kale stems and chop into bite-sized pieces. You can also use frozen kale (no need to thaw). If you’re not a big kale fan, you can always add spinach, Swiss chard, or collard greens instead. Just make sure to cook them down as desired.*****Heavy cream gives the orzo the richest, most stable consistency. Half-and-half also works, but the finished sauce will be a little lighter and less rich.
Make it dairy-free or vegan: This butternut squash orzo recipe is already a delicious vegetarian meal (provided you use a vegetarian Parmesan... yes, some Parmesan isn't vegetarian! Check the label to make sure!). To make it vegan, substitute the heavy cream with a dairy-free heavy cream alternative for the closest swap. You can also use unsweetened plant-based milk, though the result will be lighter and less creamy. Finally, omit the Parmesan or replace it with your favorite dairy-free cheese alternative.