Create a fantastic piece of evergreen content for the major areas surrounding cities you target. The content for each smaller city will be used to build out large context for the major pieces of evergreen content.
so you end up with:
MAJOR ARTICLE ABOUT EVERYTHING IN NEW ENGLAND
^stuff to do in [enter city]
^best parks in [enter city]
^top 10 restaurants in [enter city]
Over time you end up with rich major pages that target large areas - with smaller niche content that is linking to and drawing deeper context to ALL things about an area. With smart URL's and initiatives such as targeted local facebook ads propagating content - and getting local bloggers involved - it'll all be downhill from there.