Very nice, but I think there are a few things I don't like in your attempt. It is mostly the use of symbols for hills. As you see the key problem with local maps: Hill and mountain symbols could cover too big area, and at this scale the features of the hills are just as important as placement for them, this is why contours can be better in my oppinion.
Also: What is on the hills, and how roads try to follow the terrain to make sure heavy carts can reach a place without problems, etc. can be important for a map, and somehow with the exception of a robbers camp, most of your map is "devoid of life".
In my youth I spent some time near vineyards near a lake called Balaton. And I remembered that numerous buildings I see weren't that close to the roads they used to reach them, and seen several other places as well.
In other farmlands: The buildings often aren't at the entrance and aren't that close to the roads, and at this scale it can be shown.
This is something I tried to represent somehow.