I'm curious about how people slept in the longer journeys. The only thing that I've really gathered is that on the more used paths, there would be an inn about every day of travel apart, but what was the situation for roads that weren't so traveled?
Not to head off any new answers, but there are previous responses dealing with the topic of mediaeval travel. They don't directly, in most cases, talk about "sleeping rough," though, and typically focus on later periods, so more specific answers there may be welcome.
/u/sunagainstgold and others on travel with reference to fantasy literature
/u/sunagainstgold on developing travel infrastructure in the late mediaeval period
/u/sweetchilicharles on travel in England in the 13th century
/u/zither13 on the logistics of long-distance travel