That's a sharp, crisp map rwaluchow. It reminds me of some of the more recent FR city and town maps put out by Wizards--good job.

Now for the minor brickbats I like the crazy quilt patchwork of streets, it feels "natural" and organic, but there are a few hiccups from a realism standard.

The market (if that is what the circular open area on the bottom is) probably should be relocated to the east side of town--markets usually tended to be near major road and water arteries to facilitate transport. Also what is that structure that crosses the road to the west of the circle? If its a triumphal arch it probably should be on one of the larger roads or on the way to the castle. If its a gate, what is it doing in the middle of nowhere without any walls around it?

There should be a cleared area around the arena (if that is what the multilevel oval in the se part of town is). Arenas were usually major urban hubs (at least in Roman times) and had a plaza area around them where vendors could hawk food and souvenirs (not so different from today). Your arena (if that is what it is) feels kind of tucked out of the way.

At the base of the road up to the castle/citadel (I'm assuming its on a mountain or rise) there should be a cleared area or square. Also, the road going to it probably should be wider. I'm assuming the castle was built/developed first and the settlement grew up around it. That means the road to the citadel would be one of the oldest and widest.

One final thought--where's the wall? You say this is a military town. If so, it was either built to fortify a frontier or control a restive area. In either case, the lands surrounding the town would be unsettled. No wall means there's nothing to stop marauders until they reach the citadel. As I'm assuming the town grew up to service the garrison (taverns, gambling halls, etc.), I doubt they'd leave the populace to the mercies of the surrounding countryside. Thus, there should be a wall--or at least one in the stages of construction.

Obviously, one can foam at the mouth when it comes to realism, but incorporating a few principles from real cities and developments can make for a better map.

I hope you do more maps rwaluchow, you're off to a good start.