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On a spring morning in the year 2941 in the Third Age, after having goodmorninged Gandalf and having had and having joined an unexpected party, Bilbo leaves the Shire, on a quest for Erebor.

We know that Gandalf arrived in the Shire after Yestarë, Elven New Year, which was on April 6th of the Shire calendar. It was late in April when Bilbo left Bag End to join the others at the Green Dragon.

But do we have a more precise date?

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    Is your hart set on that answer for that bounty? If I were to recount the various dates and changes Tolkien went through during his writing of the various versions of the Hobbit, would it possibly contend with that answer. (If not I’ll write it anyways, just when I have more time.)
    – Edlothiad
    Commented Aug 8, 2018 at 4:39
  • @Edlothiad if you have an even better answer, then yes, please, give it a try.
    – SQB
    Commented Aug 8, 2018 at 4:45
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    I mean, it's not necessarily better then the answer in the published book. It would just have extraneous details.
    – Edlothiad
    Commented Aug 8, 2018 at 4:57

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+500

In the first chapter of The Hobbit, "An Unexpected Party", Gandalf (speaking to Thorin) says,

Thrain your father went away on the twenty-first of April, a hundred years ago last Thursday, and has never been seen by you since.

We're also told that Bilbo tended to forget things

unless he put them down on his Engagement Tablet: like this: Gandalf Tea Wednesday.

It appears to follow, then, that the Unexpected Party occurred on the Wednesday after Thursday April 21st; that is, on Wednesday April 27th. The departure, of course, occurred the next day: Thursday, April 28th.

Note: Tolkien himself did not, at least in the text of The Hobbit, pay close attention to this date (one of the characteristics that distinguishes the book from his other fiction). In Chapter 16, "A Thief in the Night", the narrator states that Bilbo

drew from a pocket in his old jacket (which he still wore over his mail), crumpled and much folded, Thorin's letter that had been put under the clock on his mantelpiece in May!

(emphasis added)

This could be considered as counting against the simple interpretation of the first chapter, or it could be simply an authorial error.

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    Things I learned today: @MattGutting is basically Sherlock Holmes.
    – Nerrolken
    Commented Oct 17, 2014 at 20:04
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    Fair enough. But even within the category of "authorial error," Tolkien's conceit of translation means it could be Tolkien's mistake or it could be "Bilbo's" in recording the events.
    – Nerrolken
    Commented Oct 17, 2014 at 20:09
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    Note that Bilbo is using the Shire calendar, while Gandalf and Thorin can't possibly be (as "April 21" (actually 21 Astron) would always be on a Friday in the Shire Reckoning. "April 21" (actually 21 Gwirith) in Steward's Reckoning (standard outside the Shire) would probably actually be 20 Astron in Shire Reckoning, because there's an inter-month day between "March" and "April" in Steward's Reckoning which doesn't come until later in the year in Shire Reckoning. (I say "probably" because I'm not 100% sure that the two years were supposed to start on the same day.)
    – Micah
    Commented Oct 17, 2014 at 21:07
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    @Micah Within the context of The Hobbit (i.e. treating it, as it originally was, as a work entirely separate from The Lord of the Rings), the Shire calendar doesn't exist; the calendar was not created until after The Lord of the Rings was written. My interpretation is that calendar references within The Hobbit are strictly to the Gregorian calendar, as readers of the first edition might expect.
    – Matt Gutting
    Commented Oct 17, 2014 at 21:10
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    @Nerrolken Given Tolkien's general method, I expect it would be both. That is, it would be an authorial error which, after published, he'd retcon into being Bilbo's slip of the pen, or some other (probably highly convoluted) in-world explanation. Except of course Tolkien doesn't retcon, he sets out to "discover" or "find out" "how it happened".
    – melissa_boiko
    Commented Aug 7, 2018 at 19:16

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