My gypsy wife sent us on a 12 state 9 day road trip from the frozen north to Florida's "Emerald Coast" and back to the still frozen North.
This was less painful than you might think; we kind of like road trips. iPhones help, but so does a cheap old two panel auto DVD player and our patented movie selection method -- parent chooses four, each child removes one until one DVD remains.
This time we tried out Google Field Trip for iOS. I won't trust my data to Google products like the comically named "Keep", but I'm relatively good with this kind of ad-supported product . Leonard has a good review up on Salon, with his take on the coverage problem we also ran into ...
... it’s not clear how in-depth Field Trip’s coverage is across the entire U.S. I used the integrated Google Maps feature to peer into some other regions I know pretty well and received widely varying results. I took a look at downtown Gainesville, Fla., and found a wealth of interesting historical information, but very little in the way of restaurant or bar recommendations. I zoomed in on Peterborough, N.H., and found zero recommendations of any kind. I checked out my father’s old neighborhood in the Upper East Side of Manhattan, and discovered much less than one would expect of one of the most densely packed regions of the world...
We had pretty good coverage of local history in parts of Illinois, but then less in Indiana and almost nothing in Kentucky. Most of the interesting alerts came from Google's use of the volunteer led Historical Marker Database; its coverage may depend on where volunteers live. I'm hoping Google will support some expansion as part of their routine Street View maintenance.
We're a long way from getting road trip history on a place like Scooba Mississippi. From the name and look of the old main street, called Railroad St, Scooba was a railroad town that died with passenger rail:
(image from Google Street View)
Now it's the home of East Mississippi Community College - which was likewise empty on our Good Friday drive by. Empty except for two police cars with closed gates on every entrance road but one. (The web pages appear to have been last revised in early 2012, but the campus is still in business. I think.)
Google Field trip was silent on Scooba. I'd like to know what it was like when times were good, and I'd like to know why students go to EMCC and what happens to them after they leave.
 Relatively good, there's still the Google predatory pricing problem. "Free" (ad supported) aps like this push better alternatives out of the market.