Preheat oven to 450 degrees F (230 degrees C). Line a rimmed baking sheet with parchment paper.

Place butternut squash into a large bowl; toss with olive oil and salt until thoroughly coated. Spread squash in a single layer on prepared baking sheet.

Roast in preheated oven until tender, about 30 minutes.

Cook sausage over high heat in a skillet until well-browned, about 7 minutes. Crumble cooked sausage into large serving bowl.

Cook apple, thyme, sage, and nutmeg over high heat in the hot skillet with the sausage grease. Stir to thoroughly brown all sides, 3 to 4 minutes. Remove with a slotted spoon and add to bowl with crumbled sausage.

Combine balsamic vinegar and maple syrup in a small saucepan. Place over high heat. When mixture comes to a boil, reduce heat to medium-low and simmer until it begins to thicken and smells strongly acidic, about 10 minutes. Remove from heat.

Combine roasted squash with the apple and sausage. Mix thoroughly.

To serve, spoon salad into individual dishes and drizzle with balsamic maple reduction. Serve with a glass of ice cold milk.