Preheat your oven to 400°F (200°C). Toss the peeled and cubed butternut squash with olive oil, 1/2 teaspoon salt, and a pinch of black pepper. Spread the cubes out on a baking sheet in a single layer. Roast for about 25-30 minutes, turning halfway through, until the squash is tender and caramelized around the edges.
While the squash roasts, bring a large pot of salted water to a boil. Add the elbow macaroni and cook until just al dente according to package instructions, usually around 7-8 minutes. Drain the pasta and set it aside.
In a skillet over medium heat, cook the turkey bacon slices until crisp. Transfer to a paper towel-lined plate to drain excess grease, then crumble into small pieces. Set aside for topping and mixing in later.
Once the squash is roasted and slightly cooled, add it to a blender or food processor along with the milk, garlic powder, onion powder, dried sage, remaining salt, and black pepper. Blend until completely smooth and creamy. Pour this mixture into a saucepan over medium heat.
Slowly add the shredded cheddar cheese to the saucepan, stirring constantly until the cheese melts fully and the sauce thickens slightly. Be careful not to boil the sauce, as this can cause it to separate.
Transfer the drained macaroni to a large mixing bowl. Pour the butternut cheese sauce over the pasta and stir gently to combine. Fold in half of the crumbled turkey bacon.
Preheat the oven to 375°F (190°C). Pour the mac and cheese mixture into a greased baking dish. Sprinkle the top evenly with the remaining turkey bacon and the bread crumbs. Bake uncovered for 20-25 minutes or until the topping is golden brown and crispy.
Remove from the oven and let it cool slightly before serving. This Butternut Mac and Cheese with Sage is perfect on its own or paired with a fresh salad for a complete meal.