I'm sure they'll fly it over somewhere deserted first - not least because they need to get confidence that it won't crash into the city! They will also want to measure enough to ensure that the sonic boom/thump is not going to break glass or do other damage. There are lots of windows in a city and breaking even a few percent of them would be very very expensive!
But once they've done that, the real goal has to be to get public support for supersonic travel. To do that they'll want to demonstrate the "sonic thump" to people, by flying over them, so people know what it sounds like and don't have the fear of the unknown that was a problem for Concorde. They will also want to be able to say to regulators and the press that they have really flown over real US cities without problems (no broken glass, no excessive complaints, etc).
Also note that the impact of a sonic boom on a city is going to be different from a cornfield - there are buildings to block or reflect the sound, and there's a higher level of background noise.
Biting the hand that feeds IT
