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Step 1
Start by preheating the oven to 425F. Using a sharp knife and a cutting board, cut the squash lengthwise all the way through. Use a spoon to scrape out the seeds and inner membranes.
Step 2
Next, brush a light coat of 2 Tablespoons olive oil, salt, and pepper onto the "meat" of the squash. Place meat side down on a baking sheet and into the oven for about 45 minutes to an hour depending on the size of the squash. You'll know it's done cooking when the outer skin is browning and becomes fork-tender.
Step 3
Flip the squash over and it should be slightly caramelized. Use a fork and/or spoon, to scoop out the inner meat.
Step 4
Cut the carrots into chunks, all of even size, and quarter the white onions with outer skin removed. Add butter and olive oil to the dutch oven over medium heat on the stovetop. Once the butter is melted, add in the carrots. Saute for 5-10 minutes until they are becoming tender. Add the onion wedges in and saute for another 5 minutes.
Step 5
Add in the cored and diced apples. As the apples begin to break down, add in the honey, brown sugar, thyme, and pumpkin spice. Stir to cook for 3 minutes.
Step 6
Add the squash and stock, starting with 2 cups of stock at first and adding more after blending to achieve the desired thickness. Use an immersion blender to smooth the soup.
Step 7
Finish by adding heavy cream. Stir and serve with your choice of toppings.