Most of the action in "Winter Dreams" takes place at the Sherry Island Golf Club. It's there that young Dexter first sees even younger Judy Jones; it's there that Dexter falls for Judy Jones a second time as an adult; it's there that Dexter sees the lifestyles of the rich and famous, which he wants for himself. Who knew country clubs were the center of so much action?
Sherry Island is actually the perfect place for this story. First, the natural loveliness of Sherry Island ties the ideas of beauty and money together in young Dexter's mind: where there's beauty, there's dough (true enough of Judy Jones!).
Second, Sherry Island allows us to imagine the class issues of the story geographically. In other words, Dexter is from Black Bear Village. We are sure that Black Bear Village is a very nice place, but it gets essentially no description from the narrator. It is a place of no importance in Dexter's imagination. On the other hand, Sherry Island – where all the rich people live – makes Dexter feel "magnificently attune to life […] radiating a brightness and a glamour he might never know again" (2.28). Sherry Island is the place where Dexter goes when he is dreaming of improving his social and financial standing.
The fact that Sherry Island is close to the place Dexter grows up reminds us of Dexter's own class background: he is middle class, but his origins are humble. He wants to spend all of his time at Sherry Island, but he can never forget that he comes from somewhere else. He does not (yet) belong in the rich world that Sherry Island symbolizes for Dexter.
The comparison between Sherry Island and Black Bear Village is similar to the comparison between New York and Minnesota. In other words, like Sherry Island, New York City (and specifically, Wall Street) represents this space of richness in comparison to Minnesota. Dexter starts off in Minnesota, but just as he left Black Bear Village, he moves on to bigger and better things. As a Minnesota native himself, Fitzgerald is highly aware of the social differences between St. Paul and New York. For more on this topic, check out our "Symbols, Imagery, Allegory" section.