The city was once of the few remaining freetowns of the Broken Kingdom. Highridge was a point of contention between the Margravate of Byrwyll and the Earldom of Alyryn, who were both trying to annex the town. The town's charter dictated that, should the kingdom of Aerlynn cease to exist, the town would become part of the principality that was closest in distance. The resulting border dispute continued for decades. Alyryn's representative in Highridge was Sir Worsley, while Byrwyll's was Lady Verin.
However, after the Battle of the Broken Kingdom, Krestia decided that the town should be awarded to the Margravate in return for remaining a staunch ally throughout the Second Grand Council and its aftermath. Highridge officially lost its freetown status on Bloomsfury 30, 2665 CE, much to the dismay of its former burgomeister.
Highridge was overseen by Burgomaster Tallyfaire, who the people regarded as a just ruler. Though it has a large population and a city wall, its standing military force was quite small. However, troops abounded from both Alyryn and Byrwyll, though the former are noticeably absent now that the city is the property of the latter.
Despite the proliferation of military might, underworld elements such as the Poison Guard grew prominent until early 2665 CE. In Phalanx of that year, the PCs arrived in Highridge and volunteered to eliminate the Poison Guard as a favor to Sir Worsley, killing the guild leader Sarshan in the taproom of The Purple Jewel.