The Sherry Island Golf Course is probably the most obvious symbol in "Winter Dreams." When we think about golf, we think about money. Belonging to a country club is a long-standing sign of privilege in American society.
Dexter goes to the golf course to earn some extra cash as a caddy, but he doesn't really need that extra dough. What he really wants from the Sherry Island Golf Club is a chance to watch the daily habits of the rich and successful. Dexter's job at the golf course provides material for his winter dreams.
At the beginning of "Winter Dreams," the Sherry Island Golf Club represents everything that Dexter wants to achieve. The golf course – and Dexter's eagerness to be on it – symbolizes wealth and high status. By the second section of "Winter Dreams," the golf course has become a transitional space where newly-rich Dexter tries to remember what it was like to be a boy caddying there. What happens once Dexter finally has the chance to golf on the course? Is it everything he'd hoped and dreamed?