Pre-heat the Oven - Adjust the oven rack to the center position and the temperature to 400°F (204°C).
Par-Cook the Bacon - Line a baking sheet with foil and place a wire rack on top. Evenly place the strips on the rack. Roast until the pieces begin to shrink and turn red, about 7 to 8 minutes. They should be flexible, not crispy. Allow them to cool until ready to handle.
Prepare the Asparagus - Wash and thoroughly dry. Trim off the tough fibrous ends to yield about 7-inch long spears. Evenly coat with olive oil, salt, and black pepper.
Wrap the Asparagus - Divide the seasoned asparagus into 8 even-sized bundles. Starting from the tips, tightly wrap one slice of par-cooked bacon around each bundle, slightly overlapping in a downward spiral. Secure it with a toothpick.
Glaze - Place the wrapped bundles on the wire rack used to cook the bacon. Brush the bundles with maple syrup if using. Lightly season with salt and pepper.
Roast - Cook until the bacon browns and crisps, and asparagus is tender, about 13 to 15 minutes.
To Serve - Remove the toothpicks and serve warm.
Notes
Make-Ahead: The bacon-wrapped asparagus can be assembled, covered, and stored in an airtight container for up to two days before roasting.
Storing: Cool completely and store in the refrigerator for up to 3 days.
Reheating: Loosely cover and reheat on the high setting in the microwave in 15 to 30-second intervals until hot. Alternatively, bake at 350ºF (177ºC) until hot.