"Screen-cap proof: Search "Woodlawn Park Amphitheatre" on Google Maps, you catch "Trek in the Park" mid-show." - Mike Russell
Right behind both the trees and that B is the actual bowl where the actors perform, so you can't see them, but there's the crowd spilling out well past the bowl. The pink truck on the left is the mobile Voodoo Doughnuts truck.
My guess is that this is Summer 2009, Atomic Arts's first year (when the troupe did "Amok Time"), because recently I checked Google Maps's view of downtown Portland and did not see Big-Ass Sandwiches at SW 3rd and Ash; that cart opened in December 2009. Maybe this is from 2009, maybe this is from 2010 when the episode performed was "Space Seed." Either way, it's cool! (And remember, this blog is about the Star Trek love as much as the Star Wars love...)