Hunting Porsches In The Wild

When Ryan and I discussed running this contest, we weren’t sure what day was best, so we chose September 30 almost at random. As it turned out, I had a really busy day, so I was only going to be able to dedicate about 3 hours to my hunt.

To prepare for the hunt, I grabbed my $100 Canon Point & Shoot, dropped the top on the 1984 V-Dub (when stalking Porsches, I highly recommend vintage VW Rabbit convertibles), and I was ready to go. As an after-thought, I also grabbed my Canon DSLR, just in case I found something interesting. My game plan was simple: point & shoot, rip & run, never get out of the car – just keep hunting, and minimize the amount of missed cars. The clock was ticking, no time to waste.

First stop on my hunt was Southport, Connecticut. While I was on my way there, heading down I-95, I saw 3 Boxsters in the on-coming lane over the course of five minutes.

No pics, didn’t happen.


I reached over and grabbed the point & shoot, and as I was turning it on a Ferrari (I think it was a 550) got on my bumper – I pulled into the middle lane, and he blew by. Just as I was about to move back into the left lane, I saw my first victim – a Carrera that was obviously in hot pursuit of the Ferrari. As he flew by, I got my first picture of the day.

Southport, Connecticut


Five minutes, four more cars. I thought I was off to a good start, but half an hour later, I hadn’t seen another one. Time to go to Westport Connecticut, which is the next town over. On my way there I saw two more, but both times was saddled with that whole shift-clutch-steering-braking thing, so I missed them.

No pics, didn’t happen.

Running Tally:
Porsches Photographed so far: 5
Porsches Seen But Not Photographed: 5

Westport, Connecticut


To all of you living in Westport, why the hell do you like Audi and BMW so much?

I spent the next half hour cruising around ridiculously crowded one-way streets, and I had NOTHING. Goose-Egg. Zip. Nada. Time to leave. No sooner had I made that decision when I saw the yellow Boxster, parked at the Brooks Brother’s store. Of COURSE!

Westport yielded only one Porsche, but it was a great picture.

At this point, I had been on the hunt for a little over an hour, and I really wasn’t getting the results I had hoped for. I decided it was time to break out the big guns, and headed to New Canaan, Connecticut. On my way there, a woman cut me off while talking on a cell phone…she was driving a Cayenne Turbo with some crazy aftermarket kit.

No pics, didn’t happen.

So, lets tally up:
Porsches Photographed so far: 6
Porsches Seen But Not Photographed: 6

New Canaan, Connecticut


This is when things really turned around for me. Six Porsches in three minutes, including two 911’s parked next to each other. But again, after driving around for five more minutes, I didn’t see any more.

Then I discovered the Metro North Railroad Commuter Parking Lot.

Six Cayennes!

After that, I was striking out, and the clock was ticking. I had found twelve Porsches in New Canaan. I left town feeling satisfied, and headed to my final destination, my ace in the hole, my…nevermind, you get the idea. I was headed to Greenwich, Connecticut.

New Tally to this point:
Porsches Photographed so far: 18
Porsches Seen But Not Photographed: 6

Greenwich, Connecticut

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This being the last stop on my hunt, I wasted no time wandering around. Instead, I went right to the main street with all the ritzy boutiques. After driving the length of just this one street – about 15 blocks long, I photographed SEVEN Porsches. At the end of that street was a parking lot, where I scored NINE more.

At this point, my point & shoot camera low-battery light kicked in, and I was pretty much out of time. On my way back to the highway, I spotted one last Porsche following me – I grabbed my DSLR, and took one Hail-Mary Picture of my rear view mirror.


Final Tally:
Porsches Photographed: 35
Porsches Seen But Not Photographed: 8

Congratulations to the Lucky Winner, Andrea who guessed 32!

Just curious – anyone want to share what number they guessed?


  1. my guess was 14.

  2. 72. I thought you would do more! Cool pics though man.

  3. Cayenne shouldn’t count!
    with the number of soccer parents out there, they must account for over 60% of porsches

  4. Jeremy, I could have done 72 just by visiting relatives and all my PCA friends, but I thought that was cheap, although according to the rules we laid out, it would have been legal – the only thing off limit was Porsche dealerships.

    Instead, I wanted to just drive around and find them at random. That’s why we used the term “in the wild”.

    I guess the previous post called “Ruthless Bookie Trash Talkin” caught you out – not that I wrote that as an intentional red-herring or anything. I’d NEVER do anything like that. I mean, posting that picture of my CVR-PCA coffee cup was just me sharing with everyone, and DEFINITELY wasn’t meant to throw you off in any way.

    Is anyone buying my load of B.S. ?

  5. Russ, I’m betting I would have had a TON more Cayenne pics, but they’re SUV’s so they just blend into a sea of BMW, Lexus etc. SUV’s…what I really needed was a wheel-man so I could spend more time hunting from the passenger seat and less time worrying about traffic.

  6. Ryan, that’s cool, we can steal my dad’s 964 and run a contest about how many tickets we can get in one day:

  7. I guessed 12, way too low, and only have myself to blame..

    My quote from the original win a porsche design blog…
    “Joe said:
    What part of CT? If you’re in the Southport area, this could be high number.”

    For those not familiar with Connecticut….Greenwich, Westport, New Canaan, and Southport are probably the four most affluent towns in the United States so I’m not surprised by the number! I live and work in the Milford area, about a half hour north on I-95 and see probably five Porsches a day tops. Then again, the per capita income is a LOT LESS. LOL

  8. Congratulations to Andrea! ..I was at 30 … close! 🙂

  9. Joe, if you live here and know all that, hang your head low, brother…12? really?

  10. just curious…besides Jeremy, did anyone guess MORE than 35?

  11. Good job Ruthless for getting all those pics. I actually guessed 41 I think, so would have been close if you hadn’t missed some others. But I also know how hard it is to always have the camera in ready mode.
    Congratulations Andrea on being the winner.

  12. Jeff, 41 was closer to my goal – I thought I could shoot 50-ish in 3 hours

  13. Ruthless, nice job on the pictures. I guessed 19, a bit low for that part of CT. If only you had not gone to New Canaan . . .

  14. Yeah, I definitely guessed 7. I was thinking more of the Portland area, but it is apparently no comparison.

  15. I am so excited to win this contest. I am looking forward to that special package arrive in the mail. Thanks Porsche Perfect, it’s been a lot of fun.


  1. 500th Post says:

    […] Hunting Porsches In The Wild – Ruthless Bookie, one of our long time readers offered to spend a day taking pictures of as many Porsches in his area as possible. We ran a little contest around it. It’s amazing how many opportunities most of us have every day to see these beauties driving around. He’s got some great pics on that post as well. […]