The first image in Winesburg, Ohio, is of berry pickers in a wagon. The last image is of a train pulling out of the station. In between, there are many references to travel, usually between countryside and town or between town and city. All of this travel is a metaphor for the modern condition, in which travel between places is easier yet people are even more isolated than they were when it was not easy to get from place to place. Anderson writes:
The coming of industrialization, attended by all the roar and rattle of affairs, the shrill cries of millions of voices that have come among us from overseas, the going and coming of trains, the growth of cities, the building of the interurban car lines that weave in and out of towns and past farmhouses, and now in these later days the coming of the automobiles has worked a tremendous change in lives and in the habits of thought of our people of Mid-America. (56)
People are much more glib than they were, yet all those words do not increase the communication between people. Instead, people do not know each other. It seems easier to cross borders, but people are much like Hal Winters and Ray Pearson-speaking to each other from opposite sides of a fence.
It seems odd that so many young men in Winesburg are in love with Helen White, given that she does not seem very extraordinary. Their love for her also seems ordinary, like George Willards conscious decision to fall in love with her. What makes her the best candidate for a young mans love? She is the daughter of a banker, and therefore wealthy and desirable.
Helen is the only suitable object of affection for a young man in Winesburg who wants to get ahead in the world. She represents all the possibilities for advancement in Winesburg, so she also represents the limits of possibilities. If she does not seem terribly exciting as a love interest, is Winesburg similarly devoid of exciting options.