Step 1

Preheat oven to 400 F.

Step 2

Prepare the acorn squash. Cut off the top and the bottom of each acorn squash to create a flat base. Keep fingers away from the knife to avoid injury. And, make sure not to cut too deep into the base of the squash. Slice each squash in half. Use a spoon to scoop out the seeds and fleshy strands tangled with the seeds.

Step 3

Place acorn squash cut sides up on a baking sheet. Drizzle the cut sides of acorn squashes with olive oil and rub the oil into the squash. Season generously with salt and pepper. Turn the squash over, and place it cut sides down on a baking sheet.

Step 4

Roast in the preheated oven at 400 F for 30 minutes.

Step 5

Make the sausage filling while the squash is being roasted in the oven.

Step 6

In a large skillet, heat olive oil, add diced onion, and cook it on medium-high heat for about 2 minutes until cooked and a bit charred.

Step 7

Add crumbled sausage, minced garlic, and Italian seasoning and cook for about 5 minutes or more on medium heat until the sausage is completely cooked through.

Step 8

Add fresh spinach and cook for another 5 minutes on medium heat until the spinach wilts.

Step 9

Add dried cranberries and chopped pecans and mix everything.

Step 10

Season with salt and pepper. Probably not necessary since the sausage is already usually salty (unless you use sweet sausage which I do not recommend).

Step 11

By this time, you have roasted the acorn squash for 30 minutes. Remove them from the oven and turn cooked squash halves cut sides up.

Step 12

Divide the sausage filling among the 4 halves and stuff the squash until the mixture is leveled or a little bit higher.

Step 13

Bake the stuffed acorn squash in the preheated oven at 350 F for 10 or 20 more minutes until the sausage mixture is heated through.