I too thought the "dead-end" character of the road to Woodhall was odd.
Originally, in the first draft, the road east out of the Woody End was a single
way that headed south of west, across the flats to the River, in distinction
from the very first map which always showed the fork and the dead end. Tolkien
failed to correct this discrepancy until the second edition of FotR, at
which point the text finally was changed to note the fork in the road, with the
main way veering north, and a little lane going down to Woodhall. "Finally",
because the published map had shown this arrangement just as the first one did.
(see HoME Vol. VI, p. 66 and p. 107 for notes on the Shire map and the Woodhall
lane.)
Since that particular feature of Frodo's route was fixed from the beginning,
one must conclude that had the Elves not come along Frodo would have gone
cross-country to get to the River in any case. Also, since there was never a
road between Woodhall and the River in Tolkien's mind, that country must be too
wet ("bogs"?) to support wheeled traffic. Thus Frodo had a difficult, wet
cross-country route awaiting him by his own choice, and the argument about the
short cut, which he seems to have decided upon while thinking during breakfast,
is moot; it seems he decided upon it the moment he took the right-hand turn at
the fork ("'That is the way for us', said Frodo." -- p.
75).

Everyone is headed for Maggot's Farm! Join us in the Reading Room this week to discuss the "The Lord of the Rings" Chapter IV: A Short Cut to Mushrooms
"I'm fond of mushrooms out of a field."
-J.R.R. Tolkien.
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