Great question. Yes!
Often times the first couple of merchants are the hardest. You're asking them to take a leap of faith and try something new that no one else in their area is yet. Typically you'll need to find a business owner that is already interested in bitcoin (there are far more than people realize!).
Once you get a couple under your belt, especially if they're rather big names, one can start using their brand to approach other businesses. "X, Y, and Z are doing it, what do you think?"
In terms of a hyperlocalized collective, the bitcoin block party on Rainey Street in Austin definitely seemed to sprout up that way. Once a few vendors in a small area (in this case food trucks) hop on board, it becomes far easier to get the rest. Then we went to the bar across the street.
We want to take advantage of this more in the near future!