The Deadwood Headdress Feather is an item that is essential when grinding reputation with Timbermaw Hold, because it is one of only two ways to get repuration with them after you get Revered with the faction. You can turn in 5 Deadwood Headdress Feather to either Grazle or Nafien in Felwood for a total of 50 reputation, meaning that each Deadwood Headdress Feather is worth 10 reputation each.
But before you can loot Deadwood Headdress Feather, you must complete a short quest to be able to loot it. Prior to this, you simply won't get any of them to drop. So how do you unlock the ability to be able to loot Deadwood Headdress Feather? All you need is to complete the quest called "Timbermaw Ally". You get this quest from Grazle in the very south end of Felwood, and it requires you to kill:
- 6 x Deadwood Warrior.
- 6 x Deadwoof Pathfinder.
- 6 x Deadwood Gardener.
All of these mobs are found in the Deadwood area just a little bit west of the quest giver. Out of these mobs, the Deadwood Pathfinder is the rares by far, so focus on killing this, since you are likely to kill a lot of the other two mobs before you are able to find all the 6 Deadwood Pathfinders you need for the quest.
When you are done, complete the quest, and you have been granted the ability to loot Deadwood Headdress Feather. These have about 50 % chance to drop from any Deadwood furblog in all of Felwood, so just go ahead and grind them to get the Deadwood Headdress Feather and reputation you need.
And at last, a small tip: Save all the Deadwood Headdress Feather until you hit Revered from killing mobs, because after you become Revered with the Timbermaw Hold, all mobs stop giving reputation with them, and you are left to turn in these or Winterfall Spirit Beads all the way until you get Exalted. So it's smart to save this until you get Revered from killing mobs only.