Falrun's 2e Dungeons & Dragons Create Characters RPGs PBP Pathfinder / D&D The Watcher from the Aether says...
Highway banditry is not common, but the area around Kendall Keep is considered to be on the edge of civilization. There has also been a recent war to the north that has drawn off a large portion of the Yeomanry's forces, reducing the patrols and allowing for a little more lawlessness than is usual.
The time of year is mid spring so no special gear is necessary.
Because you are acting as guards, you would have all of your gear equipped.