Before the war, Whitetail woods was a forest of tall trees, likely maple. Many of the trees had tubes and buckets attached to collect sap. A dirt road ran through Whitetail woods which was used as part of a racing event known as the Running of the Leaves. The Running of the Leaves was held in the fall, the racing ponies caused the leaves of the trees in Whitetail woods to fall. Applejack and Rainbow Dash competed in the Running of the Leaves as part of a grudge match the two had, over Rainbow Dash using her wings to cheat during the Iron Pony competition.
During the War
It is likely the Running of the Leaves was still continued during the war, much like Winter Wrap Up which had Pegasi pulled from the front lines to help clear the snow away. After The Last Day, Celestia fled Canterlot and took out her anger and grief over Luna's death on the megaspell missiles still falling. The missiles hit Whitetail woods, causing the forest to become extremely poisonous.
The Whitetail woods are one of the most notorious regions of the Equestrian Wasteland. The environment is extremely poisonous, even after 200 years and hostile to regular forms of life, it is unknown if any creatures reside within Whitetail woods.
Depictions in Other Stories
|Whitetail woods in Fallout: Equestria - Audio Files Series|
In Brittleshine's Quest Audio Files, it has been renamed Losttail Woods by the hellhounds. It gets its new name because after Gradens cleared it of radiation, the hellhounds tried to claim it. Of 2 packs sent in only one dog, Fleamutt, returned. It is supposedly haunted by the pre-war urban legend The Hedgeling Filly.