Bridgehampton Raceway?
Yes, it is Bridgehampton Raceway...the frst purpose-built road racing facility built in the United States. The bridge in post #19 is the Pulaski Skyway in Newark, New Jersey, about 70 miles or so from Bridgehampton. Bridgehampton must've been America's Zandvoort...right on the ocean.
The original puzzle image is of Joe Weatherly negotiating the course in 1963. Bridgehampton closed in 1999; there was talk a few years ago about reopening, but nothing came of it.
Well done!
Dan