Sauron doesn't know where the Shire is?

We read that when Sauron learned about the Shire from Gollum, that he sent his agents out to find out where this place was. One agent went to the Lonely Mountain and asked the dwarves about it. I find it difficult to explain how it could be that he *doesn't* know where it is! After all: -

1) The Great East Road goes straight through the middle of the Shire. Dwarves have been using this road quite a lot. Elves headed to the Havens use the road.

2) Sauron would be interested in knowing which elves had headed into the West. One obvious way of keeping tabs on this would be to post spies to watch the main road to the Havens. Surely his spies would know about the Shire?

3) The Shire is not a new place. AFAIK it has been around since the Witch King - nearly two thousand years. Surely the Nazgul would know about the Shire - I assume he studied maps of the region he was invading!

Thanks for the help!

[PaleStar]

I could be short and say, "because the story would be a bit shorter if they did". But I'm going to try to answer your questions.

I do not think Sauron would concern himself with where the elves were going if he was trying to rebuild himself and his power. I think that he made note of it, and perhaps thought it weakened the armies that were against him.

The Shire itself has been around for a quite a while; but even if it had been subject to the Witch-king's troublemaking(which it wasn't), the Witch-king would perhaps forget because of the wraithing process?
Besides, and I'm not too sure how accurate I'm being here since I'm shaky on the history and I don't have the book in front of me, I think the Shire was 'founded'(for lack of better word) either at the tail end of the Angmar's 'life'(I mean, by this, the Witch-king rein over it) or escaped it completely. I'm not sure how correct I am by that, though.

Or maybe Sauron was just trying to be difficult. I'm not the most knowledgable person around.

See if that helps.

[Morsul the Dark]

Not quite knowledgable however

Gandalf sqays this "They barely even know of the existence of hobbits for which I am very thankful."

Also Sauron most likely only watched out for great doings and those that would make trouble for him since hobbits did very little in the way of great deeds he most likely be unfamiliar with such a place.

Also Sauron may have bin a bit of a shock seeing how far his ring had actually traveled thinking it to be in the hands of a man or an elf

[Eomer of the Rohirrim]

Morsul makes a good point. Sauron was not at all concerned with Hobbits and, even if his spies had informed him of this peculiar race of 'little men', he would have had more pressing matters to deal with.

He may well have been aware of the vast green country because of its links to the Havens, but I can believe that Sauron only gauged from this that the Shire was north and west somewhat.

Remember that Sauron did not know what 'Shire' meant at all. It could have been anything from a huge kingdom to a single house.

[Boromir88]

Eomer and Morsul both are right, and he's an argument to support your statements. Sauron only went to the Shire to find the ring, since that was where it was. Once he finds out the ring has left the Shire, we don't hear of anymore Black Riders, or Sauron's servants being around. Showing he had no care for the Shire he only went there to find the ring, once the ring left he didn't care for it. With Saruman it was quite different, he lusted for the Shire.

[dancing spawn of ungoliant]

1) Morsul and Eomer have said pretty much all I was about to say, but I'd like to underline the fact that the hobbits really didn't make a fuss of their doings.

When diving on a highway one passes many towns and parishes but if one isn't already familiar with those places, he or she seldom pays attention to the names of the places ergo one doesn't remember them afterwards. But if some sort of celebrity comes from the certain place you drive by, you might remember the place's name later. This may be a bad example but I think you get what I'm trying to say

2) Sauron probably knew that Galadriel, Elrond and Cirdan would stick around quite long and since they were the only elves he should really worry about, he maybe woudn't be so interested in, who were leaving and by witch road.

3) Well, I don't know very much about the map culture of M-E, but was the Shire even on the maps the nazgul owned? Like the maps of the hobbits were white outside the borders of the Shire, would the map makers had marked such a small splotch on their map, I wonder.