What were roads like in Medieval Europe? Were they almost nonexistent between smaller settlements? Did some serfs spend time maintaining a manor's roads as part of their labor tax, or were the roads kept functional only by the traffic that used them?

In the later Middle Ages, roads could be anything from well-paved cobblestones to...a nice suggestion.

Around Spanish cities, for example, we have evidence of construction crews hired temporarily or seasonally to build and repair roads--crews containing women and men, and even mixing Christians and Jews among the laborers! (I assume also Muslims in some places, although the article I'm thinking of here didn't mention them).

But while financial records give us a glimpse at the higher ends of things, legal records offer a rather different picture at the other. Some parts of England and France, for example, had laws that used a lot of words to essentially say: "If the road is a giant puddle or impassable mud, you can walk in the field of the farmer right next to it."

Washed-out roads also posed a drowning risk. Not a washed-out road itself, but a well, actually. Medieval wells evidently weren't marked with nice stone tops with wooden buckets. A giant pool obscuring a road and a well near a road could easily cover up the different between the two, making it easy to fall in.

Roads in some types of areas mandated special attention. Europe<=>Near East traveler Felix Fabri recounted the difference in the road quality of the mountainous Kunterweg for his two trips to Jerusalem in the 15th century. His chronicle also gives insight into some of the experience of travelling medieval roads:

[The first time], to the road's right there were very steep-sided valleys. The elevated road was narrow, with very tall rock faces on the left hand, and on the right hand a precipice. It was so narrow and dangerous that popular rhymes were sung about it.

[...] But now the duke has had the rock artfully blasted with gunpowder, removed the stones, pushed back some impressive rocks, and leveled out the uneven path at great cost.

trans. Chareyron

"At great cost," yes...but what Fabri does not say here is that, most likely, the duke was also charging a LARGE toll for access to the road--and in this case, the only road.