Winesburg, Ohio is not so much a novel as it is a series of vignettes all concerning citizens of a small town. What connects the individual chapters is that some characters reappear in more than one, and one main characterhere likely Sherwood Anderson personified as a reporter, literallyplays a role in every chapter. The book is neither a series of short stories, nor a novel per se, but something in between those two in form.
Some of the vignettes are didactic, some ineffable, & some just plain obtuse. Each chapter could exist as a standalone, but when taken as a gestalt, perhaps this continuum of feeling tone makes the book a mirror on life itself. Lots are about people feeling feckless & ultimately acting out. Lots concern outdated sexual mores. And lots read vaguely homoerotic to me...although admittedly that is most likely just how an antiquated portrayal of human relationships play on a reader in our less physically connected modern world.
That last thought is especially curious & provocative to me, as classical interpretations of this work pinpoint its major theme to be people's lack of ability or outlet for expression and the attendant loneliness & perceived isolation that come out of that. So maybe the next time you read yet another op-ed piece about how digital connections aren't as rich as actual human interaction...you should hearken back to Sherwood Anderson's time in a small town. There were people everywhere; everyone knew everyone else, knew their family, & knew their business; and solid state electronics wouldn't be invented for well over half a century. And what did people feel back then? With nary even a lesser facebook 'friend' to be found? They felt isolated & lonely.
If I'm honest, I will tell you that Winesburg, Ohio was easy to put down & hard to pick back up; I struggled with its attenuated sense of continuity. I guess the book leaves me half scratching my head & half in awe of what love there is in human connection, how ineffable it is, & the love it takes to attempt to capture that in writing. And as to my point in the penultimate paragraph above, if you want to feel less lonely, maybe, this is me.