Explore the main street in front
You started off in the general direction of the busiest street, clearly the main lifeline of the city. The crowd seems even more impossibly thicker the further down the road you go, the setting sun and growing darkness not quite an issue as large lamps and torches adorn every building, servants scurrying around lighting up for the night business.
Buildings line every single available space down both sides of the street, occasionally a branch off to a side street off to the left or to the right appears. Shops, inns, taverns, a riot of buildings available for every taste and sound that a man could ever want. A fair number of the buildings show the shorthand for rooms available to rent, a small sign with a bed and table figure on them. As you struggle through the crowd down the street, you count no less than ten different buildings with the sign, all with large gaudy signs proclaiming various apparently royal or noble clientele as if that would justify their prices.
Several smaller streets lead off the main street further down, three streets to the left side and another two to the right. You quickly dismissed the two to the right. The streets are completely empty save for soldiers and once again filled with towering manors. The three streets to the left look a lot more disorganized, the first twisting left, the second moving straight down to what appears to be another gate in the distance and the third street twists towards the main castle building. The second, straight street appear to be more of the same as the main one that you're currently on, a riot of people and buildings haphazardly crammed along the straight road. The other two leftside streets, however, look like quieter housing areas.
The intersection between the two main streets linked to the gates feature a large open square where a large market filled with traders, all of them foreign from a glance, ply their trade. Very unlikely to find what you really want right now, a roof over your head, but there might be someone that could take you in for the night?
Two inns on the main street look the most promising, located well away from the main castle and near the gate where you had came in. One proclaimed that it is regularly visited by the ambassadors of every empire in Highroad while the other claimed that it has the loyalty of a lordling of some northern duchy but neither looked well-kept and you highly doubt that anyone, much less a noble, would regularly visit either one. A night's stay couldn't hurt though, or maybe there could be more options in the other streets?
As you search, another thought entered as you consider simply going up to the barracks and see if they still take in people at this time of the night. The guard did say the recruiters wouldn't be there but the guards at the barracks might let you in to sleep for the night, you are going to sign up anyway tomorrow, its not like it would be terribly unusual.
1) Enter the "Reckless Rigging" inn.
2) Enter the "Wyvern's Embrace" inn.
3) Explore another street (specify which, left nearest to the main gate, right nearest to the main gate, first left branch, second left branch, third left branch, first right branch and second right branch).
4) Enter the open market.
5) Walk to the castle and look for the barracks.