While it once passed Castle Naerytar, Holk House, Mornhaven Towers, and Wolfhill House, all lay within the swamp by the mid–14 th century DR. Īs the Mere of Dead Men swelled over the centuries, it flooded the lands from the sea to the road, and the High Road was repeatedly rerouted further inland, but could never be moved far enough to escape the ever-encroaching swamp. However, both roads predated Waterdeep, having been develop to connect to the harbor city. The High Road was older than the Long Road, which ran from Waterdeep to Mirabar. It was roughly 100 miles (160 kilometers) between Leilon and Neverwinter and 35 miles (56 kilometers) between Neverwinter and Port Llast. Shortly afterward, it intersected with the western Triboar Cutoff then went through Neverwinter and Port Llast before coming to Luskan. įrom the North Gate of Waterdeep, it skirted Thornhold and the eastern edge of the Mere of Dead Men where it passed beneath Iniarv's Tower and beside the Sword Mountains, before going through Leilon. The adjoining Long Road separated from the High Road a dozen miles (20 kilometers) north of Waterdeep. Hence, some accounts referred to the Trade Way as part of the High Road. At its southernmost point, the High Road entered Waterdeep, where it passed through the city as one of its most important streets and continued south as the Trade Way.