Quote:
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.
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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.