Each June 16, as both my devoted readers know, I devote a post to James Joyce, whose novel Ulysses concerns a day in the life of Dubliner Leopold Bloom. The exact day is June 16, 1904, which had personal significance for Joyce, as he went out that evening with Nora Barnacle, his future wife, who permitted him considerable liberties. So, June 16: Bloomsday (meaning: Bloom's Day), the closest thing we have to a literary holiday.
Elizabeth Minkel collects here a New York-centric menu of Bloomsday activities this weekend. You can read Joyce no matter where you are, and, as Ulysses cannot be conquered in a day, I have always recommended the long story "The Dead," which brings Dubliners to a close. If you don't like "The Dead," forget about Ulysses; if you do like it, read Dubliners through from start to finish. Your reward at the end will be that you get to read "The Dead" again, and you can then proceed to A Portrait of the Artist as a Young Man, then Ulysses, then (if you're more ambitious than I) Finnegan's Wake.
For the beginner, the main difficulty of Ulysses has to do with Joyce's method. Previously, novels had always given a kind of artificial focus to human consciousness. When characteres think, it's as if they are writing essays in the style of the author. Joyce attempts to reproduce the fluidity of our consciousness-- the way in which walking down a street, for example, a store sign, or bit of overheard conversation, might set off a kind of reverie having to do with a sexual experience, or a memory from earliest youth, or an argument with one's spouse, which reverie, while in process, might take another sudden turn when a work worry obtrudes as a businessman passes walking in the other direction. You can guess how this might be challenging for a reader accustomed to friendly, omniscient narrators who responsibly provide commentary, notes, and smooth transitions.
The aspect of Ulysses that appeals most to me is the mock-heroic. Bloom's "adventures" on his day parallel those of Ulysses making his way home from war in the Homeric epic, but Bloom is no Ulysses, and it is gradually revealed that his wife is no Penelope, either. There is a literary anecdote about a young Columbia University English professor who, feeling intimidated when Lionel Trilling asked him why he thought Ulysses was such a great book, mumbled something having to do with the revolutionary technique, the stream-of-consciousness narrative, etc., etc. When he came to the end, Trilling said he thought Ulysses was extraordinary mainly because it is the first novel in which the hero sniffs his toe jam.