What did a Chapman do in medieval times?

Answer 1

A medieval Chapman was an itinerant trader. He wandered from village to village selling items he carried in a basket he carried.

I take part in 15th century reenactment and portray this aspect of medieval life and i can tell you that carrying 20 kg of stock all day is pretty tough, but good when you get a sale.

Answer 2

The word chapman derives from Old English céapmann, meaning a dealer or trader (from céap, a market).This evolved into the post-medieval idea of a chapman as a wandering trader, pedlar or tinker.

The idea of "cheap" meaning inexpensive is also post-medieval.

So in the medieval period a céapmann was any trader at a market, often offering a range of small, useful items such as pins, needles, thread, buckles, ribbons, candles, lamps and so on.