I started it a long time ago after seeing the fad erupt on BoingBoing and after PDX local phoblogger Major Clanger did a very witty one of our own MAX (of which, I'm still quite impressed, Major; you never acknowledged my compiment of you but know that I still admire your work on that map) and then dropped it for some reason probably relating to personal pressures. My bad there.
This map might be seen as version 1.0 of it; Since I wanted to bring it to a sort of finish right now, I did not rework the logo, but take it as ironic that, given who the largest employer in Salem is, that CHERRIOTS can anagram to RHETORICS. The map withal breaks the type a bit; all the other anagrammed transit maps are rail, which, of course, Salem has none of.
I did have to take some liberties. I tried to keep that restrained. The current online version of the Cherriots route map can be seen here, and from it, one can see that the extreme simplification of some of the names (the simple letter "D" for "D Street" for example), while apprpriate for the style, leave little room for anagrammatic comedy. In such cases, I included the street type (in the example I anagrammed "D STREET", making of it a RED TEST), mostly (but not entirely) including either the standard street abbreviation or as much of the full street type word as I had to (for instance, "CROSS" didn't anagram to anything, neither did "CROSS ST", but "CROSS STR" anagrammed to "CROSS SORT", which I found ineffably funny, as I've lived in that neighborhood in Salem.
Anagrams have ways well-known of delivering wild irony; I find it funny that a PORTLAND ROAD would be the hidden lair of DATA PORN LORD; I'd always suspected that CAPITOL was a C.I.A. PLOT, WHEATLAND ROAD does seem to lead to an area of HARD WETLANDS north of town; and being so long and straight, LANCASTER DR would seem to be a sort of SCALAR TREND. If, on the other hand, there are actually any LAMER COMICS living along COMMERCIAL, I have no specific knowledge.
Other liberties would be found in the route name list. I kind of played fast and loose with puncutation; to create the anagram for the 12th & Sunnyside route I left out the numbers and the ampersand and was thus able to SHUN DESTINY, and if I left the ampersand out of STATE & FAIRVIEW I was able to give it an AREA FIVE TWIST. A particularly difficult decision was with the SOUTH COMMERCIAL route; an early anagram was SCHOOLMARM CUTIE, but I went with THE CALCIUM MOORS because that has a destinational feel for it, and it's kind of surreal besides. Also, I liked the scrambling of ORCHARD HTS into TRASH CHORD so much I decided to make the route 10X the TRASH CHORD EXPRESS, it being equally absurd that there's a fast way to get to the place.