Why did Crispin and Bear encounter so few people as they began their journey?

There are a few reasons Bear and Crispin encountered few people during their journey to Great Wexley.

For one, the population of England was much smaller and concentrated in small villages during the Middle Ages. Have you ever heard the phrase, "few and far between?" This accurately describes the settlement patterns of Medieval English people. If you were traveling at this time, you could expect to come across a village or manor house here or there, perhaps connected to one another by one or two roads. Infrastructure then was not at all like it is today, and most people never even left the village they were born in! The probability that Bear and Crispin might come across other travelers was exceptionally small... but what about the villages?

I've already mentioned that villages were spread far apart and typically quite small, but one could expect that when our duo comes across the village, surely they would meet some people. Unfortunately, the plague was rampant at this time and often left entire villages desolated. Even minor illnesses like the flu posed a threat to a village, and it is estimated that around half of the population of England died during the Middle Ages as a result of the plague.

Finally, I'd like the mention the particular timing of the story. Crispin and Bear are headed to Great Wexley for the Feast of Saint John the Baptist on the 23rd of June. During spring and summer, the majority of the population would have been tending their fields, working to grow food! Subsistence farming places a lot of demand's on a person's time, so if anyone wanted to eat, they needed to be working in the fields. Even if people had wanted to leave their village, they would need enough time to do so, as well as food to sustain them on the journey.