Cook the bacon in a large skillet over medium heat until crisp, 8 to 10 minutes. Transfer the bacon to a paper towel-lined plate and let cool, then chop. Add the vinegar to the same skillet with the bacon fat, followed by the Dijon, maple syrup and a few turns of pepper. Whisk together, heating over medium heat until emulsified, then turn off the heat.
To serve, place the romaine on a platter and sprinkle with the bacon, crumbled blue cheese and dried cherries. Drizzle with the warm bacon fat dressing and season with salt and pepper.