These guides to Portland came out (mostly) annually for a long period of time and usually contained a map of Portland that showed streetcar routes as well as detailed route listings within the guide. Using advertisements in contemporaneous newspapers, we can estimate when the guides were published each year, which allows us to date the maps and route listings a bit better. The dates below are the earliest that an advertisement for each new edition has been found. The year links to the route listing if it exists within the archive.

• 1909 – June 12
• 1911 – May 14 (”Pittmon’s red guide-book of Portland is now ready”)
• 1912 – July 11
• 1914 – April 12
• **1915 –** September 19 (this edition was late, but very heavily promoted with ads appearing through January 1916)
• 1918 – May 29 (”Off the press shortly”)
• 1919 – May 15 (”Just out,” named as the eighth edition)
• **1921 –** June 1 (ad says guide will be off the press “in a few days”)
• **1924 –** April 16 (”Just off the press”)
• 1928 – June 17
• 1933 – September 21 (this edition ran late due to Portland’s Great Renumbering)
• 1937 – May 19 (”New City Guide Just Off Press”)