Home » How To Drive A Bunch Of Cool Vintage Cars For Free This Weekend

How To Drive A Bunch Of Cool Vintage Cars For Free This Weekend

Drive Fun Cars

This weekend is the Greenwich Concours d’Elegance in blue-blooded coastal Connecticut, with the Concours Sport tomorrow and the full Concours on Sunday. I went to the Sport last year with my daughter and it was a great time. If you love cars and you’re in the area, either day or both days is worth a trip. I love nothing more than chatting with owners and seeing cars I’ve never seen before. That’s not true, I love one thing more: Driving old cars.

Hagerty, which is a classic car company that’s somehow both vertically and horizontally integrated at the same time, not only runs the Concours, it also runs the Ride & Drive event that happens beforehand. Only a well-insured company like, well, an insurance company, is going to just hand the keys to a vintage Buick Super or original Ford Bronco to some random car weirdos. Thankfully, Hagerty is that company.

Vidframe Min Top
Vidframe Min Bottom

Earlier today I got to go for a spin in the vintage Cadillac they had on hand, as well as drive the Buick droptop (video coming soon). They were both fantastic. Here I am with video editor/shooter extraordinaire Erica in the back of the 1957 Cadillac Fleetwood:

1957 Cadillac Fleetwood 1

And here are some happy folks in the Bronco:


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And here are the details of the cars:

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And, finally, here’s me checking out an Audi 1000SP!

You can’t drive the Audi unless you’re the owner, but the other stuff is all driveable and it doesn’t require a ticket and you can’t reserve in advance.


If you want to participate just arrive as early as you can on Saturday, June 1st or Sunday, June 2nd, and get in line. It’s first come, first served from 9 am to 3 pm each day. And did I mention it’s free?

Go have some fun and drive some cars. Then go look at some cars.

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16 days ago

This is an excellent idea. If I knew ahead of time, I’d definitely try to make it to an event that had test drives of classic cars.

Jack Trade
Jack Trade
20 days ago

I enjoy how they’re all autos; as cool as it is, Hagerty is still wise to your “yeah of course I can drive stick” bluster.

20 days ago
Reply to  Jack Trade

Not their first rodeo…

Luis Lopez
Luis Lopez
20 days ago

So, I saw the headline and clicked because I thought to myself, “Hey, I did that last year when I brought my GTI to the Radwood show on Saturday at the Greenwich Concours.” I waited in line for a few minutes and got the chance to drive the light blue 1971 Bronco….

Lo and behold, as I read and scrolled down the article, I saw a picture of me in the driver’s seat about to embark! LOL!

It’s worth doing, as all it takes is a driver’s license, and the car train goes through a park and the downtown of Greenwich. You end up going no more than about 40 mph in one stretch, but it was cool to make believe, if only for a little bit. And, on that day, there was also a McLaren and Ferrari to drive.

As for the driving experience in that 1971 Bronco. Very cool, very nostalgic with that super thin steering wheel, but the “steering” was merely a vague idea, and the driving position was strange. I’m 6’3″ and it felt like the wheel was in my chest and I could’ve used much more seat track travel!

20 days ago

Man. I’d love to scoot around in that Buick and that Caddy. Actually they’re all pretty awesome, and they must have fantastic old car smell.

20 days ago

That looks like an excellent time! Any ideas if they’ll be doing this again at a more midwestern locale? I’d be more than happy to take a day and road-trip several hundred miles for a chance at driving that Fleetwood.

Good on Hagerty for setting this up – a short drive behind the wheel of something unique can easily be enough to set the hook for a future-enthusiast.

Looking forward to the video!

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