Preheat your oven to 400 degrees.

Slice open your acorn squash, and scoop out the seeds. Brush with 1 tablespoon of the olive oil and sprinkle with salt & pepper. Roast for 20-30 minutes until fork tender

Meanwhile, saute up your filling. Heat 1 tablespoon olive oil in a saute pan. Saute the mushrooms on medium heat, for 3-5 minutes. Add in the pork sausage and cook for 5-7 minutes, making sure to cut up the sausage into small pieces with a wooden spoon.

Add in the diced apples and cook till soft but still crisp, about 3 minutes, then stir in the chestnuts. Cook till sausage is fully cooked and no longer pink and the chestnuts are heated through, about 3-5 minutes. Season with salt & pepper.

Scoop the filling into each acorn squash and enjoy!