Confession: I’m not a classic car guy but I’ve always wanted to be a classic car guy. As long as I can remember I’ve had this goofy daydream of working on a classic car in my garage. I bet you’ve had it too:
Garage door up. Work bench. Peg board full of tools. A sweet, powder blue ‘72 Ford Mustang Coupe in the driveway. Hood up. The inline six engine is bare, needs a little work. You’ve got a cold beer open on a stool. Some music’s going. And you’re tinkering. Some tightening here. Tweaking there. Working on your car. Livin’ the dream…
That’s it. Nothing fancy.
Just you and some grease on your hands and oil on your jeans in your favorite old, faded t-shirt and a ride you take pride in restoring. Maybe a neighbor walks by and asks what you’re working on. You tell him, “The cylinder heads are warped so I’m checking the damage with the feeler gauge” and you actually know what all this means. Your neighbor walks up the driveway. Peaks his head under the hood. You offer him a beer. He accepts. You talk engines. It’s awesome.
If you already have this, congratulations. You’re living the classic car dream (and send me a pic of your garage). If you don’t, and you’re interested, you’ve come to the right place.
Currently, I have neither the space nor the time to live this dream. But my mind wanders to it more than it ever has before. I think it’s because I don’t like new cars very much. I hate the push-button start. I hate the giant LCD screen in the dash. I miss real odometers and speedometers and CD players. I miss specific knobs for treble and bass. I miss a car looking like, you know, a car.
Now the outside of every car looks like a 1990s wall phone with headlights and the inside looks like a smart phone. I want to spend as little time on my phone these days as possible and I especially don’t want to drive one. In the very near future, all cars will have a remote kill switch and facial recognition software and you’ll be spied on every time you get behind the wheel. That sucks. No guy wants this, but it’s inevitable.
The solution? Classic cars. Old school. Off the grid.

An older guy in his late 70s a few streets away has a set-up like the one I just mentioned. He’s a Corvette guy. He has a huge Corvette emblem on one wall of his garage, shelves of tools and posters and framed photos of famous Corvettes, most of which I’ve never heard of. It’s incredible. Also, he’s not super friendly. I pass him when I’m walking the dog on the weekends and he’s usually working on his car. It’s a yellow 1990 Corvette ZR1. The color is actually “competition yellow”. Those are the only two things he’s ever shared in years of me walking by his house.
And that’s fine. I get it. The garage is his time. He doesn’t need to host some random guy classic car fantasy camp just because I walk by every now and then.
The only other thing he mentioned a few weeks ago was that if I liked classic cars and vintage cars I should go to a place called Ragtop Motorcars not far from us.
So I went. For me. For you. For all of us. The place rules. It’s a museum and showroom and hangout for vintage/classic car guys. I could stay there all day and a huge shout out for the tour and talk!
Here Are 5 Things I Learned:
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First, until you’ve strolled a giant showroom of beautifully restored cars you really can’t appreciate how exceptional these cars are and, in contrast, how boxy and unimaginative just about every new car is. So many cars in the 50s through 90s had character. The brands were distinct. The designers seemed to really try. Now with few exceptions, every car or SUV looks exactly the same.
Second, the hobby is not as expensive as I thought. Yes, you can drop six figures (or millions!) on rare models and fully restored whatevers, but if you have the space and the time and you want a ‘56 Ford Thunderbird or an ‘88 Corvette that are both in great shape, they can be had for between $20k-$30k. I don’t know why, but I thought it would be a lot more.
(NOTE: I’m using vintage and classic interchangeably. I know there’s a difference, but for our purposes, we’re just talking about cool old cars)
Third, I never knew how insurance on these things worked. I thought if you bought one and wanted to drive it, you had to take out a full insurance policy on it like it’s a new car. Turns out, you just take out a mileage policy and it’s not that expensive. One thousand miles a year for X dollars.
Fourth, the classic car world is very social. There are Camaro clubs and Thunderbird clubs and Pontiac GTO clubs and it’s all super cool. These guys get together on weekends or at events or shows and shoot the shit about their cars. What they’re restoring. How they’re restoring. Cars they have their eyes on. What cars are in which movies. It’s a club, basically, for dudes who like cars. What’s better than that?

Five, there are several layers to this collecting game. From old guys who have kept just one car for forty years to guys who only have that one sweet ride they’ve dreamed of since they were seventeen in their garage to the super rich guys who have a collection. Now, I’m not saying I’ll ever have a collection or a dedicated building for my cars like Jay Leno, but the “basic very rich guy” level of cars is something to behold:
There are these giant warehouse looking places where it’s just a row of fifteen or twenty custom built garages where rich guys store their cars. These garages can be tricked out however they want. Some have full bars. Others have full mechanic set-ups. Some look like a sports bar / man cave. But ultimately, it’s a gated, security-guarded spot with a few dozen bays of garages filled with vintage cars where guys go to see their collection, joy ride and hang out with other wealthy guys who have five plus vintage rides they don’t keep at home.
Sounds amazing.
As for me, I’m still not at step one yet. Like I said, there’s not much time or space at my place for tinkering or extra cars, seeing as my daughter will likely be getting her first in the next year or so and then my son after that.
But I love all of this. And I know the exact ride I’ll buy to restore when the time comes: a ‘94 Ford Bronco. Eddie Bauer version if I can get it.
Until then, I’ll go annoy my neighbor or chat up my new buddy at Ragtop.
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Jon Finkel
Editor-in-Chief, Midlife Male
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