Oh my goodness, what have I done? Is this a picture with no fully legible signs or license plates. Let the challenge begin.
But, before guessing, keep in mind that you might be able to guess the right city, but have the wrong state. So to win a drink on me, I'll have to have both correctly attributed in the answer.
That's all the hint you fools are getting for now.
Toby gets it... again.
Now another picture of Portland, ME featuring an extra serving of MILF: