Lay out bacon in a cold cast iron skillet and cook over medium heat until crispy on both sides. Remove bacon from the skillet and place on a paper towel lined plate to cool.
Cut off any remaining root from the bottom of the iceberg and remove the outermost leaves. Rinse and pat dry, then cut the head into four equal wedges and place on separate plates.
In a small bowl, whisk all dressing ingredients together and season with salt and pepper.
To serve, spoon dressing over wedges and top with crumbled bacon bits and cherry tomatoes.
Garnish with any remaining blue cheese crumbles, herbs, and salt and pepper.