Using a sharp knife, cut each end of the acorn squash (removing as little as possible) to create a flat surface. Then, slice the squash in half and scoop out the seeds using a spoon. Repeat with the other squash. Brush the halves with olive oil and sprinkle with salt and pepper. Roast in the oven for 50-60 minutes until the squash is tender.
While squash is baking, heat 1 tbsp of olive oil in a large skillet over medium-high heat. Add the ground turkey and cook until meat is cooked through. Sprinkle with salt and pepper. Remove from pan.