Depends where you're coming from. If you're in LA and you need to get to Bridgeport in a hurry, of course you're going to take a nonstop flight to JFK and then rent a car and drive the hour and change to Bridgeport. If you're going from Davenport to Derry, you're almost certainly going to fly from the Quad Cities Airport through Chicago to Logan. That much, I'd agree with.
There's certainly some degree of Derry-to-Boston commuting going on, at least judging by drivetime traffic on 93. There's some degree of Bridgeport-to-NYC commuting going on as well, though Bridgeport has a much larger local economy of its own (especially when you include the rest of southern Fairfield County in the mix) than does Derry.
For radio, Bridgeport is its own Arbitron market, separate from NYC - but three of the top ten stations in the Bridgeport ratings are NYC stations. Derry is just outside the Boston Arbitron market, but most of what's audible there comes from either Boston or Manchester.
For TV, Bridgeport is at the edge of the NYC Nielsen market, while Derry's solidly within the Boston Nielsen market, since that market includes most of New Hampshire.
And where WBIN is concerned, none of that really matters. Anyone who's actually watched the WBIN newscast (which I suspect excludes most of the participants in this thread) know that from 1000 miles away in Iowa, they're trying to play both sides of the fence: the news open includes both Boston and Manchester, the screen behind the anchor displays Boston landmarks, the weather forecasts are for both Boston and Manchester, the headline ticker at the bottom of the screen is Boston headlines from the Globe, and the stories come from both sides of the state line. Since the station's OTA signal is almost nonexistent, it's dependent on cable and satellite for most of its potential audience, and it's on cable across most of the market (including Boston proper) and on satellite across the entire market, from New Hampshire all the way out to Cape Cod.
One suspects that's a recipe for obscurity, in the end: the attempt to serve Boston dilutes the New Hampshire part of the product enough to guarantee WMUR continued leadership on that side of the border, and the newscast simply doesn't have the resources behind it to be a credible alternative to WFXT, WSBK/WBZ or WLVI/WHDH at 10 for viewers seeking a Boston newscast.