1 delicata squash, halved lengthwise and seeded
2 teaspoons olive oil, divided, or as needed
2 apples - peeled, cored and diced
¼ cup diced onion
1 clove garlic, minced
½ teaspoon finely chopped fresh rosemary
1 pinch ground cinnamon, or to taste
salt and ground black pepper to taste
2 slices bacon
2 tablespoons goat cheese
Preheat oven to 400 degrees F (200 degrees C).
Brush inside surface of delicata squash halves with about 1 teaspoon olive oil; place on a baking sheet.
Bake in the preheated oven until tender when pierced with a fork, about 30 minutes.
Heat remaining 1 teaspoon olive oil in a skillet over medium heat; cook and stir apples and onion until onion is translucent, about 5 minutes. Stir garlic, rosemary, and cinnamon into apple mixture; season with salt and pepper. Reduce heat to low; continue to cook, stirring occasionally, until apples are tender, about 5 minutes.
Place bacon in a skillet and cook over medium-high heat, turning occasionally, until crisp, about 8 minutes. Drain bacon slices on paper towels.
Fill delicata halves with apple mixture; crumble bacon and goat cheese over apple mixture.