I ran an ad in a local paper that was also used for other small town papers. It was one of those free newspapers that are thrown on lawns once a week. Our paper is called the "Twin-Boro News" and covers three towns. There are other papers throughout the county that cover a certain area under different names. It was a quarter of a page, ran for one month, but never got a response.
I also opted for one month in a paper magazine called "ParentPaper". It's a free paper that circulates in a bin at Barnes & Noble, other bookstores, libraries and schools. I recieved one commission from it. The best thing I got from it, was that the client was president of a mortgage company and gave me a great deal on a re-finance.
I tried it again, and nothing. This is an area where they can easily afford portrait art. Chances are potential clients are having their nannies look thru the local papers while they look thru the Wall Street Journal. There's also a strong chance that Madonna's nannies looked at it.
I was thinking about running another month before a holiday, but I had started working seriously on my drawings. I make enough at the tattoo shop and did'nt want the extra stress.
Good luck.