Obtaining a presence via mobile kiosk near Portland's tourist epicenter was great strategy for Know Your City; they'll be there (along with a few other tour-oriented agencies) to help answer that "What do we do now?" post-Voodoo conundrum faced by so many of the city's visitors. The upcoming roster of tours includes a few of particular appeal (DIY Portland, Multicultural Portland, "Parklandia" (oof), and the Dirty Side of Portland), and they've also announced two one-off tours happening the third weekend in June.
One of them should be like catnip to foodie visitors: the Food Cart Revolution bike tour on Sat, June 21. Part of Pedalpalooza, it's free (though limited to 40 people) and led by Cartopia: Portland’s Food Cart Revolution author Kelly Rodgers, who should be able to explain the phenomenon of micro-entrepreneurship better than most, cruising past carts and pods from downtown on into North Portland. (Complete info here.)
The following day's Lost South Portland tour on Sun June 22 is a bit more of a mystery even for someone who's lived here for a while (they're still keeping the "Your" alive in their name):
Although today it may not be readily apparent, South Portland has rich, fascinating and contested history that is all but little-known to many Portlanders. In the early 1900′s, thousands of Jewish and Italian immigrants settled in close-knit community, with Kosher butcher shops, Italian delis, benevolent societies, bocce ball courts, and a religious life that boasted seven synagogues and an Italian church. By the late 1960’s, the area turned into Portland’s counter-culture epicenter, with coffeehouses, folk music and bygone business such as the beloved Psychedelic Supermarket, which provided political information and free food to area youth.
This one's being led by author and historian Polina Olsen with a contribution from Richard Falaschetti, and while it's not free, $17 pre-sale is a good price for someone to tell you something you don't already know about the city you live in (or like to visit). Info here.