In a large pot, cook pasta according to package directions. Drain.
Cut bacon into strips and cook bacon in a non-stick skillet cook bacon until crispy. Remove bacon from pan, and set aside on a paper towel-lined plate.
In a food processor, add all the ingredients for the dressing and process until smooth, if your dressing is too thick, thin it out with some milk or water. Salt the dressing well.
In a large bowl, toss cherry tomatoes, arugula and penne with the dressing. Top with bacon, parmesan and more freshly cracked black pepper.