Preheat the oven to 400 degrees F. Toss the squash, bacon, sage and 1/4 teaspoon each salt and pepper on a rimmed baking sheet. Roast, turning once, until the squash is tender and the bacon is crisp, 20 minutes.
Meanwhile, fill a small bowl with ice water. Bring a small saucepan of water to a boil. Hold the whole chives together with tongs and dip in the boiling water 30 seconds. Remove and dip in the ice water to cool, then remove and drain on paper towels.
Whisk the chopped chives, vinegar, olive oil, and salt and pepper to taste in a large bowl. Add the squash-bacon mixture, the turkey, pear and kale; toss. Season with salt and pepper.
Warm the tortillas in a dry skillet over medium heat, 30 seconds per side. Spoon one-quarter of the turkey-squash mixture down the center of each wrap. Top evenly with the gorgonzola and nuts. Roll each into a cone shape and tie closed with a whole chive.