Ahh, yes. This is Autopuzzles where things are rarely as they seem, right? The first notion for someone heading NW of Bridgeport would be Buffalo, where Pierce-Arrows were built. And the the 1911-1913 Pierce-Arrows are very similar in appearance to the puzzle photos. Only a small problem. If one were to "shuffle off to Buffalo", one would have to shuffle for about 420 miles. A bit of a long shuffle.
However, along that general route, one might just shuffle through Poughkeepsie, NY, which is roughly 70 mile NW of Bridgeport. And in Poughkeepsie, the American Fiat was made between the years of 1910 and 1917. I've attached a photo of one. Not my photo, but one I found on the web. I found very little about American Fiat, other than some info stating that they were very large cars with an 8.6 liter six-cylinder motor and brakes on the rear wheels only. Scary as hell if ya ask me. Ohh...and there are only 10 of them known to exist today.
If I didn't hit the bullseye with this one (and thanks to your clues, I've learned a lot)...well, I photographed a car show this evening and shot it all in RAW format...a new venture for me. I'm gonna have to do some trial and error to see which method of editing them works best. I prefer Corel's Paint Shop Pro Photo for several reasons, but it's very slow in dealing with RAW images. I guess I'll have to bite the bullet and see if Photoshop CS5 does any better; another thing, the computer I'm doing the editing on is a pretty hefty one...4 dual-core processors with 16 gb of ram and a whole buncha disk storage...and an SSD for the operating system. But the RAW handling in PSP seems to be able to suck up as much memory as a single application is allowed to do, based on the way I have it configured (to run as a server, rather than a workstation...it actually runs at its best that way.) But I ramble.
I better get to work editing photos.
RtR