The Duskendale road is a road which connects Duskendale in the crownlands with Maidenpool in the riverlands. Near Duskendale the road runs between Blackwater Bay and low limestone hills. Fishermen use the road to bring their wares to market. The road forks at the Hollard castle about an hour north of Duskendale, with the main road continuing on through fields, hills, and woods to Maidenpool and another branch heading northeast to Crackclaw Point. The road is rutted and twisty near Maidenpool.
A Storm of Swords
Brienne of Tarth, Ser Jaime Lannister, and Ser Cleos Frey find Maidenpool to have been sacked during the War of the Five Kings, but the land becomes green again half a mile on. Brienne plans to travel south on the Duskendale road and then continue on the Rosby road to King's Landing. As they ride past a trampled wheat field and a stone wall near Maidenpool, the travelers are attacked by outlaw bowmen and Cleos is killed. After the outlaws disappear, Jaime duels Brienne on the road, among trees, and in a shallow brook in an attempt to win his freedom. Their duel is interrupted by the Brave Companions, however, who take the pair captive.
A Feast for Crows
Brienne travels from Duskendale toward Maidenpool during her search for Sansa Stark, and she purchases clams at a fishing village on the road. She encounters Podrick Payne at the Hollard castle and allows the boy to join her quest. The road becomes emptier as they travel farther from Duskendale, and inns they pass have been sacked or have been occupied by soldiers. When the pair near Maidenpool, Brienne looks for the spot where she and Jaime had been captured by the Brave Companions.