I recently found copies of the first two volumes of James E. Thorold Rogers’ A History of Agriculture and Prices in England (the first two volumes cover 1259-1400).
The background is built from USGS GTOPO30 data, imported into Profantasy’s Fractal Terrains, coloured using the Terraformer add-on.
I then brought the map into Campaign Cartographer 3 and added the locations, borders and all the other vector stuff.
The highlighted locations are where the travellers stopped for the night; other locations are those mentioned on the journey.
The journey took a total of seven days, because the travellers rested for an extra day in Thirsk.