There used to be a lot of activities that took place around a populated area like a village or town, which you would encounter before you reached the town itself. Most of those crafts have either been eliminated in the developed world or now take place out of view on private land, and so modern authors don't think of them when creating fantasy worlds or writing historical fiction. I think that sprinkling those in could both enrich the worlds you're writing in and, potentially, add useful plot devices.
For example, your travelers might know that they're near civilization when they start finding trees in the woods that have been tapped, for pitch or for sap. They might find a forester's trap line and trace it back to his hut to get medical care. Maybe they retrace the passage of a peasant and his pig out hunting for truffles. If they're coming along a coast, maybe your travelers come across the pools where sea water is dried down to salt, or the furnaces where bog iron ore is smelted.
Maybe they see a column of smoke and follow it to the house-sized kilns of a potter's yard where men work making bricks or roof tiles. From miles away they could smell the unmistakeable odor of pine sap being rendered down into pitch, and follow that to a village. Or they hear the flute playing of a shepherd boy whiling away the hours in the high pasture.
They could find the clearing where the charcoal burners recently broke down an earth kiln, and follow the hoof prints and drag marks of their horse and sledge as they hauled the charcoal back to civilization. Or follow the sound of metal on stone to a quarry or gravel pit. Maybe they know they're nearly to town when they come across a clay bank with signs of recent clay gathering.
Of course around every town and city there will be farms, more densely packed the closer you are. But don't just think of fields of grains or vegetables. Think of managed woodlands, like maybe trees coppiced-- cut and then regrown--to customize the shape or size of the branches. Cows being grazed in a communal green. Waiting as a huge flock of ducks is driven across the road. Orchards in bloom.
If they're approaching by road, there will be things best done out of town. The threshing floor where grain is beaten with flails or run through crushing wheels to separate the grain from its casing, and then winnowed, using the wind to carry away the chaff. Laundresses working in the river, their linens bleaching on the grass at the drying yard. The stench of the tanners, barred from town for stinking so badly. The rushing wheel-race and great creaking wheel of the flour mill.
If it's a larger town, there might be a livestock market outside the gates, with goats milling in woven willow pens or chickens in wooden cages. Or a line of horses for the wealthier buyer or your desperate travelers. There might be a red light district, escaping the regulations of the city proper, or plain old slums. More industrial yards, like the yards where fabric is dyed (these might also smell quite bad, like rotting plant material, or urine).
There are so many things that preindustrial people did and would find familiar that we just don't know about now. So much of life was lived out in the open for anyone to see. Make your world busy and loud and colorful!
This is a big reason that I have always loved the Brother Cadfael novels, set in the mid 1100s. Written by Ellis Peters, each book has such a vivid sense of the place and the time period. Many different settings around Shrewsbury are described, along with the people and their various jobs.
I love that kind of world building and would add that many resources were tightly regulated that we don't consider nowadays. Examples are the right to herd your pigs in an oak forest belonging to a specific monastery (saw an example where an altar piece had a carved pig to make sure the claim was known and advertised) or down to which farmers had the right to tree leaves in the fall (shortage of other animal bedding in certain Swiss valleys). The idea of a wilderness in a medieval setting is not what we think.
Great points! Thank you.
Forever recommending A Collection of Unmitigated Pedantry as an introductory resource for this! The author is a historian of the ancient mediterranean and he has a lengthy two-part blog post on "lonely cities": how fictional cities tend to look in pseudomedieval fantasy versus how real cities actually worked, specifically how they reshaped the land use for many miles around. Part I, part II, or available read aloud on YouTube here.
