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Only two dates out of this five-day period of travel earn entries in the Tale of Years:
October 1 — ‘Gandalf leaves Bree.’
October 3 — ‘He is attacked at night on Weathertop.’
The narrative agrees that October 3 is the evening on which Gandalf is besieged by the Nazgûl, because he scratches a ‘G’ rune plus three marks — for the third day of the month — on the rock that Aragorn finds on Weathertop.
Finally, October 5 is named in the narrative itself: ‘By night they had reached the feet of the westward slopes, and there they camped. It was the night of the fifth of October, and they were six days out from Bree.’
Working forwards and backwards in the narrative from these three anchors, we can supply all five days with events. The adventures of Gandalf happen offstage, but he later recounts them at the Council of Elrond.
Before dawn, a company of at least five Nazgûl fling down the west-gate of Bree, gallop through town, and head east along the Road. Gandalf leaves the Prancing Pony and rides out after them on Shadowfax.
Strider and the four hobbits begin their second day of hiking through the Chetwood. They have been swerving to avoid pursuit, but now start taking paths that lead more directly east.
They leave the Chetwood ‘On the third day out from Bree’. Counting September 30 as their first day out and October 1 as their second day out, this must mean they leave the Chetwood on October 2.
Strider and the hobbits reach the edge of the Chetwood and walk out into the open country. The ground here is lower than in the Bree-land behind them, and is beginning to get boggy.
The hobbits and Strider camp, now several miles inside the Midgewater Marshes. They are swarmed by insects as they try to sleep.
Sam wonders, ‘What do they live on when they can’t get hobbit?’
‘The next day, the fourth, was little better, and the night almost as comfortless.’
Strider and the four hobbits spend a second day picking their way east through the Midgewater Marshes.
All nine Nazgûl are now gathered at Weathertop. Sensing Gandalf’s anger as he rides towards them, they abandon the hill to the wizard while the sun remains up.
Gandalf and Shadowfax reach Weathertop and climb to the crown of the hill. The Nazgûl surround them as the sun starts to set.
The overnight battle between Gandalf and the nine Nazgûl is witnessed by Strider and Frodo — without their knowing it — from where they sit awake in their camp near the Midgewater Marshes.
Gandalf takes his stand in the ruined ring of the fortress of Amon Sûl. The nine Nazgûl move forward in the dark and begin their attack.
Frodo and Strider, awake in their camp two days’ march to the west, see lightning leaping into the sky in the direction of the Weather Hills.
With the approach of dawn, the nine Nazgûl end their overnight attack. Gandalf cannot now search for Frodo without leading the Nazgûl to him, so the wizard rides north, away from the Road. Four Nazgûl ride after him.
‘They had not gone far on the fifth day when they left the last straggling pools and reed-beds of the marshes behind them.’
Strider and the hobbits reach the eastern edge of the Midgewater Marshes where the land begins rising. The hobbits see the Weather Hills for the first time, standing ahead of them along the horizon.
‘It was already night when at last they halted and made their camp under some stunted alder-trees by the shores of the stream.’
It’s already dark when Strider and the four hobbits finally stop, camping beneath alder trees on the banks of a small stream that runs down from the Weather Hills. For the first time on their journey they set a watch.
‘Next morning they set out again soon after sunrise.’ And here we reach the explicit October 5th reference mentioned at the top of the page:
After another day’s hike—their sixth since leaving Bree—Strider and the four hobbits reach the Weather Hills and camp where their slopes rise abruptly from the plain. For a second night in a row they set a watch.
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