There was a map thread going where folks posted their maps and how they made them. It appears it got lost to the forum upgrade, so I'm going to get it started again.
Here's one I finished this evening for the campus rec department at my old university. Click the thumbnail for the full res version (600dpi, 8 1/2 x 11)
I used my Garmin Oregon 450 to collect multiple GPS tracks of the trails and then hand drew the trails in Topofusion. I made a .kml file for web display first and then converted it to shapefile format because there was an unfulfilled need for a printable map. I added attribute data to the shapefile about trail difficulty, which I used to set the symbology. Labels were converted to annotation in ArcGIS 10 so they could be individually manipulated and placed along the trails (and roads).
Streams, contours, and 10m DEM hillshade came from statewide datasets. The roads came from the city GIS database. I did not want to use the road centerlines files available from the state. What I had to do was use the parcel data and dissolve all the parcels together to highlight the roads. Road labels came from the road centerlines TXDOT files. Then I added the green layer with 80% transparency to show the university property the trails are on.
ArcGIS would not let me use the pictographs in the legend to represent linear features (the pictographs are easy to understand and correspond to signage on the trail which includes the symbol and the trail name). So when I completed the map, I exported it as a .pdf and opened it with Inkscape, an open source vector drawing program. The symbols were ESRI fonts and once I found them with the character map, it was easy to delete the linear symbols ArcGIS wanted to use and replace them with the icons that I wanted in the legend.
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Thread: Map Thread