Avoiding the Old Forest...?

[Inziladun]

Originally Posted by Sardy

When leaving Crickhollow for Rivendell, it's clear that the Hobbits wanted to remain undetected and therefore chose to avoid Buckleberry (the assumed first destination of the Black Riders) and didn't want to be seen crossing the Brandywine Bridge. By necessity Frodo wisely chose to stay off the main road and avoid the North Gate. It's also clear that they are hoping (even expecting) to meet Gandalf on the East Road.

Why then wouldn't Frodo, et al, simply use the Tunnel Gate under the Hedge and---rather than entering blindly into the Old Forest---simply follow the narrow clearing between the east side of the Hedge and the Old Forest. This seems to be not just easier terrain to traverse than the Forest (and even the places where the Forest meets the Hedge would be easier to circumvent via brief sojourns into the woods than to stake their entire jourey through the dark forest) but is also a more direct route to the East Road.

As the dialogue among the Hobbits as they stood near the gate indicates, they anticipated no real difficulty in getting through the Forest, despite the warning of Fatty Bolger. The cover of the trees might have seemed appealing to them as well.
Also, It doesn't seem that any of them had ever been much beyond the borders, other than into the Forest, and they may not have had a very clear idea of the exact track of the Road after the Brandywine Bridge. They knew though, that going through the Forest and veering east and slightly north was sure to lead them to it.

[Rumil]

I thought the hobbits were worried that the Nazgul would break through the gate at the Brandywine Bridge and be waiting for them if they ventured directly onto the East Road.

[Bêthberry]

Well, early on in "Three is Company" Gandalf advises Frodo to travel:

Originally Posted by Gandalf

"Towards danger; but not too rashly, nor too straight, . . "

Following the hedge would have been too straight, perhaps.

[The Mouth of Sauron]

The same kind of idea has often come to my mind for their journey from Tom Bombadil's house to the Road.

Why didn't they just keep to the eastern edge of the Old Forest ?

[William Cloud Hicklin]

Of course, the real answer is that at the time Tolkien had no idea where the story was going, but since Bombadil and Willowman already existed he had ready-made plot to use.

There wasn't even any geography at the time, beyond what he had just invented for the Shire and Buckland. All he had was The Hobbit's vague given of a Road that eventually reached Rivendell. He never actually did get the two books to line up , even though he tried in LR 2d Ed (as Fonstad and CT discuss)- this may lie at the root of his latter-day insistence on drawing the map first!

[Rune Son of Bjarne]

That might be the answer to why Tolkien wrote it that way. . .but it does not answer why the hobbits chose the rute they did.

I see it like two very different discusions.

[Kuruharan]

they anticipated no real difficulty in getting through the Forest

Speaking strictly within the confines of the story I agree with this to a large extent, although Merry at least had some ideas that the Old Forest was more dangerous than your typical wood.

It doesn't even seem that any other idea besides plowing right through the wood was considered.