If a town hasn't been modernised since medieval times it will be very dilapidated.
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Medieval towns were crowded because serfs wanted more freedom and moved out of the manor land to towns.
Some medieval towns transportations were wagons or carriages. Some people just walked.
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Many medieval towns were clean by their standards, which would have meant uncluttered, without foul odors, and so on. The medieval people did not understand anything about bacteria, viruses, and disease vectors, so in some modern senses, the towns were not clean; for example you could not trust the water.
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