I've been wanting to go old school & draw some maps by hand... Something like you might see on the first page of an adventure novel. I've found next to nothing on the web and am hoping that one of you has (or has seen) an ancient cartography text that describes the basics. If yes, please reply with author/title so that I can narrow my search.
Here is a good website with some tips on hand drawing shaded relief maps of mountainous areas. It is worth checking out.
This blog entry has several links to creating different aspects of hand drawn maps. She mostly links to Fantastic Maps, which looks pretty interesting (the author actually created the maps for the Game of Thrones books). For example, this one on how to draw a town is pretty good. You might also want to have a look at Cartographers Guild which has a lot of hand drawn maps. However, it appears that many are actually drawn in Photoshop. But it looks as if there is at least one tutorial.
While not really a useful resource, this is a fun website.
Finally, there are a lot of different types of maps. Each would have their own methods. For example, are you drawing a world map? A map of a country? A town? A street? A fantasy map? Colour or black and white?
Are you looking to do a fictional place? Or are you looking to do a map on a real place?
If it is based upon a real place, I recommend that you developed the basic line work in something like QGIS from data available and then utilize GIMP (Photoshop) or Inkscape (Illustrator) to manipulate it into the hand drawn look.
This is a vast assortment of tutorials out there on both programs that utilize filters and other techniques to get a sketchy appearance.
I might also add the forum Carto Talk which is a great resource for information on cartographic design. Prior to web-mapping-services and after the computer put an end to doing everything by hand, cartography was typically created (and still is largely) in Adobe Illustrator and Photoshop. Illustrator is used for its robust vector editing and typography tools, Photoshop typically for editing shaded reliefs.