Preheat oven to 375 degrees, line a baking sheet with foil or parchment paper, and set aside.
Trim and quarter your Brussels sprouts and place in a medium bowl. Add olive oil, salt, and pepper, and toss to coat. Spread out on prepared baking sheet and roast for 30 minutes.
Meanwhile, cook your bacon in a medium skillet over medium heat, stirring occasionally, until browned and crisp. Remove to a paper towel-lined plate to drain grease.
During the last 15 minutes of the Brussels sprouts roasting, remove the baking sheet, add the apples, and return to oven for the remaining time.
Once the roasting is complete, remove baking sheet and allow to cool slightly. Then add veggies and bacon to a large bowl, add red wine vinegar, and toss or stir to coat and you're ready to serve!