Why does Dexter find spring dismal and the fall gorgeous and full of hope?

Dexter's "winter dreams" all have to do with the acquisition of things, and he never really appreciates anything until he owns it. When he finally gets Judy Jones and realizes she is not what he thought she was (she is not actually "the best"), this causes him to question his entire view of life. The fall, when Dexter can reflect on his summer experiences, becomes a time of nostalgia for what might have been but was not.

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Dexter finds the spring "dismal" because it means he must return to his work as a caddy, and abandon his "winter dreams." The fall, however, is "gorgeous" because then he can reflect on his "fleeting brilliant impressions" of summer and imagine himself, for example, a champion golfer, easily able to defeat...

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the wealthy men for whom he caddies.

These "winter dreams" all have to do with the acquisition of things. The narrator explains that: 

He wanted not association with glittering things and glittering people—he wanted the glittering things themselves. Often he reached out for the best without knowing why he wanted it—and sometimes he ran up against the mysterious denials and prohibitions in which life indulges.

Another way to understand the "dismal" nature of the spring is to associate it with the "mysterious" denials of real life. Dexter is a person who seems able to make his dreams come true; he becomes wealthy very young, and soon is living out his fantasy of playing at the club where he once caddied. Yet Judy Jones is one thing he cannot have. She is his most persistent "winter dream," a vision of loveliness that, like a dream, consistently eludes him. The reality of Judy is a bit more complicated, however. Whether Judy really is "the best" or not is beside the point—for Dexter, she is one of those "glittering things" he wants, and his inability to get her points out his own emptiness. The fact that Dexter desires her but cannot have her suggests that the "hope" he finds in the fall could be as empty as the "dismal" spring. 

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In "Winter Dreams," Dexter loves the fall because it allows his imagination fuel powerful dreams that cannot be envisioned in the spring.

Dexter finds the fall's "full of hope" animating his dreams.  In the fall, Dexter's dreams define his existence.  He trembles with anticipation and excitement at these aspirations.  Dexter is able to "make brisk abrupt gestures of command to imaginary audiences and armies."  He is able to envision how he is the golf champion at the club, and how he is able to attract admirers.  The fall is where his dreams come alive.  

However, in the spring, Dexter's reality emerges as a caddy.  His daily life as a caddy who does his job well fades in comparison to the life of dreams that he sees in the winter.  In his work as a caddy, he is not able to command the attention of everyone in the club, and he lacks the elements that serve as "ready grist to his mill."   The gulf between reality and dreams is the reason why Dexter finds the spring so vastly different than the fall.  Dexter's "Winter Dreams" can only be seen at a time when reality does not interfere with them, and represents why he sees the fall's hope as superior to the dismal reality of the spring.

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