Here's a really neat idea my friend Lenore turned into reality.
She has been living in a place called "The Five Towns" on Long Island for over 40 years (Lawrence, Cedarhurst, Woodmere, Inwood and Hewlett). All the shopkeepers there know her personally. She approached almost all (or maybe all) of them and offered them advertising on her web site. She put up a really nice website called http://www.thefivetowns.com and has a complete guide to all the shops and services in The Five Towns there. It doesn't hurt that it's a relatively upscale neighborhood. In order to put together this site she had to do alot of leg work. She went from store to store with her laptop and showed the storekeepers a preliminary design of her site. They all knew her (for years) and therefore trusted her. She advertises for them on her site. They're happy with the increase in patronage and she's happy with the increase in $$$$. There is alot of other information available on the site that interests community members and visitors - listings of real estate, houses of worship and services.
She advertises her site (very cleverly) in the local supermarket circulars.
Smart Cookie, my friend Lenore.