Darkshire and Raven Hill were not always as they were. Before the first war, the two towns bustled with trade and were some of the liveliest of towns in Elwynn Forest, Grand Hamlet and Sunnyglade. Sunnyglade was told to be of the most beautiful of locales in the kingdom where many amorous couples ventured to host their weddings.

Grand Hamlet's relative location.
This all was changed during the events of the First War. Sunnyglade was quickly deserted as its inhabitants sought shelter from the marauding Orcish Horde - and ogres quickly took up its ruins as their new Home. The nearby mage tower known as Tower of Azora was overrun by orcish warlocks who sought the secrets of Stormwind's conjurers. Grand Hamlet was razed to the ground in a decisive battle, forcing its defenders to retreat into northern Elwynn. As Karazhan's corruption sapped the land of its life, the once-sunny forests of southern Elwynn blackened and twisted into what is now Duskwood.
Permanent damage was done to the land, and only when the Alliance of Lordaeron retook the kingdom did its former inhabitants attempt to resettle the province. Grand Hamlet was rechristened as Darkshire and Sunnyglade was renamed to Raven Hill to reflect the gloomy fate of the land.