Wherein medieval mail carriers let nothing stay their appointed rounds—except for the possibility of a quick buck.

Several months ago our neighborhood’s mail carrier retired, forcing the postal service to find a replacement. In the interim between the previous carrier and our new carrier, this meant a series of fill-ins who were required to navigate our rural area—frequently with mixed success. For a few weeks it was common to see neighbors wandering the road carrying mis-delivered envelopes and packages to the correct address. Fortunately, our run of Cliff Clavins ended with a regular carrier who is capable of the complex task of matching the house number on an envelope with the number on a mailbox.
As seemingly unendurable as we found our journey in the postal wilderness—what is the point in living if I need to wait more than two days for my Happy-Cola gummies?—reliable mail delivery is a relatively recent development. In the Middle Ages letter writers needed not only to find someone who was going to the recipient’s area, but also would be willing and able to safely deliver the mail without trying to turn a profit.
Return to Sender
While some readers might find even the process of writing a simple email to be too laborious (why type a bunch of words when you can just text a poop emoji to express your thoughts), medieval letter writing involved not only the difficulty of finding someone with the literacy needed to write the letter, but also the expense of paper and a seal to authenticate the document. Still more, the writer needed to find a way to actually have the letter delivered.
There were three general ways of delivering documents and packages. First, for those with adequate household staff and money, either a servant could be sent to deliver the item (this required a staff large enough to be able to spare the servant for the possible months of delivery time) or a messenger could be hired. For those with less means, a carter could be employed to carry their mail as one of the items on his cart (as a sort of proto-UPS driver, but without the brown shorts). Other people would simply rely on friends or family, or pilgrims, to carry mail to a location to which they were already traveling.
All this meant, of course, that it could take a substantial amount of time before someone could even be lined up to carry the mail. One of Sir John Falstoff’s servants wrote in 1448 to explain that it wasn’t his fault his correspondence was late because “if messengers to London could have been found before Christmas, the letters were ready to go.”
Once a mail carrier was arranged and sent on his or her way, however, there was no guarantee that locating the recipient would be an easy task. Well-to-do medieval property owners tended to move between several estates, meaning a messenger might need to travel between several distant homes before finally delivering the mail. Deborah Thorpe, for example, notes, “One letter written in 1450 to the chaplain of Caister Castle in Norfolk gave no less than three alternative points of delivery for the bearer to try if the chaplain was not to be found at the castle.”
Please Read the Letter
Even putting aside the difficulty of finding a person to deliver the mail, there was still a high possibility of the package not reaching its destination. Accidents or bad weather could result in mail being lost or destroyed, bandits might steal the package (or one’s enemies could deliberately steal a letter looking for valuable information) or, perhaps worst of all, the mail carrier might intentionally mis-deliver the mail for personal profit.
An example of this can be found in Chaucer’s “The Man of Law’s Tale” from The Canterbury Tales in which “this messager, to doon his avantage,” delivers letters announcing a royal birth to the queen’s enemy (who just happens to be her mother-in-law). The messenger used the conflict to his advantage, working the angles with his mail delivery until the king discovers the trickery and has his conniving mother executed (we don’t hear what happens to the mailman, although he probably wound up in a particularly unpleasant Dead Letter Office).
Image: Royal 10 E IV f. 3v (Source).