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The most famous of the Dalelands, Shadowdale’s notoriety would appear to be at odds with its pastoral lifestyle. It is a quiet, wooded land of dense forests and prosperous farms . and it happens to be home to a surprising number of very powerful and important people. The reputation of Shadowdale’s residents has spread from the Sword Coast to the farthest reaches of the Moonsea.

Of all the Dalelands, the land of Shadowdale is the most common stop for parties of adventurers. The town has long looked to adventuring companies for security and leadership. A large number of ancient ruins, accesses to the Underdark, and hidden treasure caches ensure that most heroes will find something profitable and useful to do in Shadowdale.

Shadowdale lies along the road from Shadow Gap to Voonlar, controlling a major trade route from Cormyr to the cities of the Moonsea. Most people are familiar with the town of Shadowdale, but the greater portion of Shadowdalesmen live as independent farmers and homesteaders in the open lands northeast of the town.

Shadowdale stretches almost 100 miles from the Dagger Hills to the Elvenwoods, and is more than 30 miles wide. Like Mistledale to the south, the Dale’s lands of the Dale have open since before humans came to Cormanthor. Unlike Mistledale, the lands of Shadowdale are broken by large areas of light woods and rolling hills.

Most travelers come to Shadowdale along the Shadow Gap-Voonlar road, but major trails lead south along the Ashaba to Mistledale and west through the Dagger Hills to Daggerdale. The trails have not been very safe lately, with raiders and brigands reported in the area.

Besides the town of Shadowdale, there are no other communities or villages of note. However, there are some large, remote family freeholds that are home to as many as 20 to 30 kinsmen. These freeholds are usually known by the name of the family: Blackcreek Crossing, the Shallain Hold, and so on.

In recent years, Shadowdale has been the Dalelands “front line of defense” The Dale played a part in the alliance against Lashan of Scardale, and contributed forces to King Azoun’s crusade against the Tuigan Horde. Most importantly, the Dale fended off a major Zhentish invasion during the Time of Troubles. Shadowdale has also been faced with a number of troubles of its own. In 1339 DR, the ruler of the Dale, Lord Aumry, was assassinated. The warrior Jyordhan captured and executed the murderers, but was later revealed to be a Zhentarim agent. He ruled with a heavy hand until 1345 DR, when he was slain by the mage Khelbun Arunsun of Waterdeep.

Shadowdale was leaderless for three years, although Jyordhan’s heir Lyran Nathander claimed the throne. In 1348 DR, the rightful rule of Shadowdale was reestablished by the Knights of Myth Drannor. Doust Sulwood, one of the adventurers, became Lord of Shadowdale and ruled for five years. His successor, Mourngrym Amcathra, has ruled since. He defended the Dale against the forces of Lyran the Pretender in 1357 DR and against the Zhents during the Time of Troubles, in 1358 DR.

Inns. The only inn of note in Shadowdale is the Old Skull Inn, a respectable and reasonably-priced establishment. Rooms range from 2 sp to 5 gp per night. The Old Skull is also the only taproom of the village.

Supplies. Jamble has a 50% chance of stocking any particular item in the PHB price list, and a 20% chance of stocking a weapon. His prices are at a 15% markup. Weregund the Trader charges PHB prices and stocks most everyday items.

Watch. No formal watch organization exists, but the locals can summon 2d6 guardsmen from the Twisted Tower within d6+2 rounds.

Temples. Shadowdale has temples of Chauntea, Tymora, and Lathander.

Other. Shadowdale is home to Elminster the Sage. Elminster rarely receives visitors and is often away from his tower for extended periods.