Looks like it could be San Francisco? There are other hilly towns.
It also looks like it could be a trick shot with the different light exposures and the line near the middle. The "car" is quite interesting. There appear to be two unusual touring cars with top down (how often do you really see that in era photos?). They both have an unusual style trunk on the rear (unusual) and a front fender mounted spare tire (commonly done in horseless carriage era and again in the later '20s, but although done, was not common from the time this photo would appear to be). Even the clothing and hats are very similar if not the same in the two cars.
Another observation. It should appear that the closer car is going down hill? But the crowd of people and one car that can barely be seen at the edge of the picture would indicate that the car could not have just driven by (they could not have filled the street that quickly). Also, in the photo, the spokes of the wheels are clearly visible, something unlikely with the slow films of the day, if the wheel was turning.
I suspect that it was a "trick-shot" showing the one car chasing itself.
Although the scene appears to be staged (at least to me), I would say that it was not professionally done because of the light exposure error.
Someone somewhere must know what is going on with this? I await other explanations and theories.
Thank you Jay for another good one!
Drive carefully, and enjoy, W2
And why is that man chasing the car down the hill?
This seems to be a frame from the Harold Lloyd comedy "Hot Water."
Downtown Seattle has a few hills like that !
Rick is right, the sequence can be seen at about 3:45 in this link: https://www.youtube.com/watch?v=Yh3Ooj_njRM
It's Harold standing there, looking at his runaway car after he pushed it a little bit too far..
(He did catch it - in the movies anything is possible )