Brookline Boulevard, known simply as “the Boulevard” in the neighborhood, is the broadest commercial street in Pittsburgh—which surprises visitors from flat cities, where it would be at best a middling business street. It’s a curiously one-sided business strip: almost all the businesses are on the southwest side, the northeast side being primarily residential.

That may be because, for much of the neighborhood’s life, it was effectively two streets. When trolleys ran in Brookline, Brookline Boulevard was two narrow strips for cars, with trolleys in a separate median in the middle—much like Broadway in Dormont along the current Red Line. Removing the trolleys and paving the median created the exceptionally broad street.

The Brookline business district is one that is seldom thought of as a destination for shoppers from out of the neighborhood. But it should be. It has very few chain stores, but it is prosperous enough that storefronts are seldom empty for long. The result is a delightful mix of little one-off shops, cafés, and ethnic restaurants.

The tower in the distance is the lookout tower of Engine House Fifty-Seven.