http:// www.mvderby.com/pdf/58thDerbyBooklet.pdf
Old pic.
According to this article, this is Maggie Nixon. It's the cover of the 2013 Vineyard Seadogs calendar. I'm going to take a big leap and assume that the dog is her pet.
http:// www.mvtimes.com/2012/08/08/noteworthy-events-marthas-vineyard-11866/