Hi Nicholas,
Where will you store the information necessary for Numbers to calculate these results?
If it is to be a direct calculation of the shortest distance, you will need the geographic location of each of the two cities, plus a formula/algorithm for calculating the great circle distance between those two locations. For Boston-New York, that's about 190 miles.
For Driving distance (215 miles), the calculations are somewhat more complicated. They require access to a large data set comprising a 'routing map' for the area you want to include, then an algorithm that can look up the two cities, determine a driving route between them, find the driving distance for each section of that route, and add them up.
If you place a severe limit on the number of cities, and have access to the 'driving distance' grids that were (and may still be) included with printed paper maps from service stations and/or AAA (in the US), CAA (Canada), the AA (in Britain) and other motorist organizations elsewhere in the world, you might be able to handle this with one or more Lookup tables, and a suitable lookup function in column C.
Otherwise, you could hire Google's development team (or one of several others) to reinvent the wheel, so to speak, and provide you with a standalone application to do this.
Or you could choose to use a more suitable and existing tool. Some choices are MapQuest, OpenStreetMap, Bing Maps, Google Maps, or (Apple) Maps (included in recent versions of OS X).
Regards,
Barry