Preheat oven to 350 degrees. Cut Brussels in half, and dice bacon. Set aside.
In a large glass bowl, whisk together the bourbon, maple syrup, olive oil, vinegar, and paprika.
Add Brussels to bowl, with marinade, toss to coat and let sit for 15 minutes. Stir in bacon.
Spread Brussels on large, foil lined baking sheet. Season with salt & pepper.
Roast on low oven rack until tender on the inside and crispy on outside, about 30-35 minutes, stirring occasionally. Glaze should be thickened when done, and Brussels slightly charred.