If I didn't know better I'd say that's 57 Lima Bean ( aka the Drunk Monkey ) on the hill in the background. He's had his '57 a long time, but not that long lol. 
Hmm, I see a '55/'56 ragtop and a '58 2dr post...but no '57. That's minus 2 bonus points for this post  

TomP is the track expert. He could probably tell you what track it is just by the color of the dirt. Cool picture though. That Starliner really looks good with that bronze paint and 5 spokes! I love these old pictures.