I would have done it all in GIS software (QGIS most likely) myself using shapefiles from the County/State/Town, but I suppose that depends on your preexisting knowledge of GIS software and access to high quality data. I

In order to look good, it would probably also require some substantial design work in the symbology of the layers you're using.

EDIT: Another commenter suggests OSM, and yeah, that would be way easier than starting with shapefiles for various features.