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Preheat the oven to 375 degrees. Bring a large pot of water along with the vinegar to a boil over a high flame. Lightly oil a baking sheet. Starting at the base of the asparagus and working up, wrap each with a piece of bacon in a spiral and place on the baking sheet. Repeat with the remaining asparagus and bacon. Roast for 30-40 minutes until the bacon is crisp and completely cooked.
Meanwhile, when the water is fully boiling, reduce the flame to medium-low. Using a wooden spoon, carefully stir the water to create a vortex. Crack an egg into a small bowl, making sure not to break the yolk. Pour into the center of the boiling water. Repeat with the remaining eggs. Continue to simmer until the whites are completely opaque and the yolks are slightly firm, about 4 minutes for medium. Remove gently to a bowl with a slotted spoon. Divide the asparagus evenly between 2 plates and top with the poached eggs and a pinch of salt and pepper to taste.