slang Someone who observes a construction or demolition job with great interest from a vantage point outside of the job site, such as the sidewalk. There was a whole crowd of sidewalk superintendents gathered around to see the historic theater being leveled to the ground. Apparently I was quite the sidewalk superintendent as a child, spending hours watching construction crews go about their business.

The act of skateboarding, or an instance of such, especially when used as transportation rather than for doing tricks. The older people in my neighborhood give me funny looks whenever they see me out sidewalk surfing. This town is known for its sidewalk surfing. In fact, you tend to see more people going to work on skateboards than on bicycles.

Someone who rides a skateboard, especially as a means of transportation rather than to do tricks. This town is full of sidewalk surfers zipping by on their way to class or work. I used to be a sidewalk surfer when I was in college, but after breaking my ankle I never got back on a board again.