Notably, cyclist associations were instrumental in advocating for road conditioning in the late 19th century and early 20th, both in the UK [0] and the USA [1], and maybe elsewhere.

[0] https://en.wikipedia.org/wiki/Roads_Improvement_Association

[1] https://en.wikipedia.org/wiki/Good_Roads_Movement

The Romans had roads... So did the Greeks, who also produced the Antykethera mechanism (precision machining)

But not the roads very suitable for bicycles. Even modern bikes are not exactly nice on many stone roads. Now remove air-tires and every little bumb will be felt.

I've read that penny farthings are great for bad roads though. One article mentioned they lost control and wheeled over a kerb without a murmur. you couldn't do that on a safety bicycle.