Arrange asparagus on a rimmed baking sheet. Drizzle with olive oil and toss to coat. Season with salt and pepper, to taste.
Gather the asparagus into 6 equal bundles. Wrap each bundle with one slice of bacon. Place the wrapped bundles on the baking sheet.
Brush the bacon with a little bit of maple syrup on top.
Bake for 20-25 minutes, or until the asparagus is tender and the bacon is crispy. The total baking time will vary depending on the size and thickness of your asparagus spears.
Notes
To cook the bacon wrapped asparagus on the grill, preheat the grill to medium heat. Secure the bundles with toothpicks so that they don't fall apart when turning. Grill the bundles (covered) for 12-15 minutes, turning occasionally.
Cook the asparagus bundles in a large skillet on the stovetop. To do so, heat olive oil in the bottom of the skillet over medium heat. Arrange the asparagus bundles in the skillet and cook until the bacon is crisp on one side. Flip the bundles over and continue to cook until the bacon is crisp on the other side, and the asparagus is tender. You'll likely need to do this in batches, so that the asparagus bundles fit in a single layer in the pan.
Sprinkle the bacon with brown sugar instead of brushing with maple syrup.
Garnish with grated Parmesan cheese, lemon wedges, a drizzle of balsamic glaze, or fresh herbs, if desired.
Trim the tough, woody ends off of the asparagusstalks before assembling the bundles. To do this, bend the asparagus spears gently with your forefinger and thumb (the spot where you feel the stalk naturally snap is where the woody end starts); or you can use a knife to cut off about 1 inch from the end of the asparagus.
Use center cut bacon, not thick-cut bacon. The center cut bacon becomes crispy sooner in the oven, and is less greasy than its thicker counterpart.
Scale the recipe to serve the size of your group. For instance, double all of the ingredients and prepare 2 lbs. of asparagus. Similarly, you can cut all of the ingredients in half to serve just 2-3 people.
The total cooking time will vary depending on the size and thickness of your asparagus spears. You'll know the dish is done when the bacon looks crispy and the asparagus is tender.