Cool Rides The most memorable drives

The most memorable drives

Cool Rides

The stickers on this 1956 Chevy wagon (seen here at Motorland in Arundel) tell the whole story, says Cutlip. “I’ve been everywhere, man.” Photo by Will Cutlip
Photo by Will Cutlip


The best car I ever owned was a mint-green, ’82 Saab 900i that my ex-wife and I bought in 1988. It had a non-turbo 16-valve engine, which meant that it only had a top end of 175 mph instead of the 217 mph the turbo models were capable of. But this also meant that it didn’t have to go into the shop three times a year at the outrageously inflated repair rates the Saab people charge.

And it also came with a Blaupunkt sound system, which kicked out something like 120 watts RMS and either improved or degraded gas mileage performance, depending on whether you set the fader to the front or rear speakers. It was a lot of car; it was sex on wheels; it was a magic carpet.

We had been driving a ’72 Oldsmobile Cutlass, which was also a bit of a road rocket, being a fairly light vehicle powered by a gnarly 350 cu. Rocket V8. That was a fun car, but it didn’t take much to steal it—a toddler with a butter knife and a bad attitude could drive it away in seconds. It was, in fact, stolen from us three times, the last on the night before our wedding. So when the Saab appeared a few months later, we jumped.

When I started looking for teaching work, we had been living in Providence, Rhode Island, and I decided I really didn’t want to teach there. I had seen “Blackboard Jungle” a dozen times, and I wasn’t craving the urban educational experience, so we started looking at Maine.

We had been to Maine once or twice—indeed, we had honeymooned on Mount Desert Island—but hadn’t really considered living here. Then I heard about a job as a writing teacher in Mars Hill, way up in The County, and so I tossed the suit and a bag of sandwiches into the Saab, and jetted up I-95 for the interview.

I knew that Maine was a pretty place. I knew all about “the rocky coast of Maine,” about Mount Desert Island, about Route 1 and its fabled roadside attractions, the bargain barns and the lobster shacks, all of that stuff. What I was not ready for was Aroostook County in potato blossom time, for a gently rolling landscape carpeted in large, yellow flowers, framed by green hills and low mountains, and stretching out as far as the eye could see.

It was a revelation, a profound beauty that no one seemed to know about. I felt like I had discovered a new country, another place entirely, a quiet place bathed in yellow light and blessed with clean, clear roads.

And in that moment, in that car, on that highway, I fell in love with driving in Maine. It was not the postcard perfection of Route 1 overlooking Damariscotta, but an entirely hidden Maine, with its own secret highway, free of traffic and road signage. I didn’t get the job, but I drove away a richer man. There would be similar moments in subsequent years, but that was the one the really took my breath away.

And that, I will contend, is what driving is all about.


I took my first drive through Ontario when I was in high school. My friend Beth had been given a new Fiat Spyder convertible for her 16th birthday, which is a heck of a nice gift—her parents were both doctors and often tried to make up for their scarcity in the home by buying their kids a lot of stuff. But there were a couple of hitches with this car: One, Beth couldn’t drive a stick, and two, she hated driving in the first place. And this was a problem, because she had fallen madly in love with a guy she had met on a trip through upstate New York, and she just had to see him again.

So she told her parents she was staying with friends across town for a couple of days, and I told my parents the same thing, and then we jumped in the Fiat and took off from Michigan for New York.

I hadn’t been driving that long, and I had never covered any distance in a car equipped with a manual transmission, but I felt I was up to the task. I was 16 and had been driving my brother-in-law’s Volkswagen bus under his direct tutelage and was doing OK. But there were some distinct differences between the two vehicles, the main one being, when you step on the gas in a Fiat Spyder, something happens. And it was my first long drive of any type, and I had not been aware of the lure of speed, of what happened when you merged with your vehicle and forgot about speed limits and just went for it.

And Ontario is a great place to do that. If you look at a map, you’ll see that the fast route to New York from Detroit was through Ontario. And it is a material fact that, during that time, the early ’70s, Ontario didn’t really have a budget for enforcing highway speeds. They put up signs saying, “Speed monitored by aircraft,” but that was a ruse, like those unmanned black-and-whites the police park near highways to deter speeders. I didn’t really know this at the time, and I really didn’t think about it. What I was mostly aware of was, Wow, this is fun!

And it was. Say what you will about the ’70s Fiats—they didn’t last, and they definitely weren’t made for traversing snowy highways rendered less slippery by steel-eating salt. But boy, are they fun to drive. You don’t so much get in them as strap them on, and a little speed gives you a giant thrill. On this particular trip, I kept it up around 100 mph most of the way. We were not alone in this, but we pretty much passed everything else on the road. The 401 went by in a couple of hours, the Queen E way in a matter of minutes. It was a heck of a ride.

We had a fun stay in Buffalo, met some great people, came back tired but satisfied. The only glitch in the trip was when we tried to get back into Detroit from Windsor, Canada. The border patrol took one look at us and pointed to a well-lit parking space: Over there, hippies, and don’t try anything funny.

We did what we were told. They didn’t find anything, because there was nothing to find. But this didn’t deter the border patrol. Okay, said the guy in charge, now we’re going to do a cavity search.

Oh, we said. Cavity search? What’s that?

They told us, but they never got around to doing it. We laughed so hard at their explanation that they finally just ordered us into the car and told us to get the hell out of there.


There’s a reason there are so many songs about driving in California: The place is made for it. It’s where most upscale auto ads are filmed, because the countryside is just so knock-your-eyes-out gorgeous, and there are so many roads that wind and climb and open up onto fabulous vistas. I spent most of 2015 there, ferrying art supplies between the Bay Area and Mendocino County, and I saw a lot of beautiful country.

It’s also the worst place to drive in a lot of ways, a Darwinian-Skinnerian nightmare governed by the survival of the rudest. And the worst place of all to drive a car in my opinion is the city of San Francisco.

One day, I was asked to drive a load of art supplies to a studio in Frisco for a friend who decided she’d make a better navigator than a driver. She told me to keep an eye out for Gough Street.

“Golf Street?”

“No, Gough, gee-oh-you-gee-aach. The studio is a block south of Gough.”

Traffic was, of course, terrible, but I had no trouble finding the street. And there was only one way to go, and that was up.

It’s really hard to exaggerate how steep Gough Street is. It’s maybe 50 blocks from the foot to the summit, and if you dropped a bowling ball when you got to the top, it would roll downhill for a half hour or so and hit the bay at just under the speed of light. Most of the roofs in Maine are pitched more shallow than Gough Street. It really is that steep.

And we were driving my friend’s VW Golf, which was a nice, staid, boring little car equipped with a manual transmission. And this was my first trip up Gough Street.

We did pretty good for about 40  blocks, and then got caught behind an SUV driven by a person who wasn’t real clear on which road she wanted to make a left on. There are stop lights on Gough Street, which seems to me to be a crazy idea, and this person was pulling up to each one in succession, looking down that street, and moving on just before the light changed.

Our luck held until the very last light just short of the top. The woman in the SUV looked down that street, hesitated, let a car pass, and made a left—just as the light changed.

And there we were, stuck at the top, waiting for the light to change. And when it changed, I stomped on the gas and let off the clutch, and stalled. And stalled again. And stalled again. And the horns were blaring, and I pretty much figured the San Franciscans were going to get out of their cars and tear us apart. The train behind us stretched all the way to the bottom of the hill.

“I’ll drive,” shouted my friend, and so we executed a hasty change of seats. She was able to get us moving, for which I was grateful, but I never want to go back.

But Highway 101 is another story. If there is a heaven for car fanatics, it’s that drive north to Ukiah through Santa Rosa and wine country. There isn’t a prettier road in America, especially the part that follows the Russian River, a scene out of “Lord of the Rings,” but with grapes instead of orcs.

Today, vast stretches of Highway 101 have been marked by fire. The beauty of Santa Rosa has been replaced by a war zone, a blasted, blackened landscape that was once lush and green. It will be a long time before that beauty comes back, but I hope to see it again one day, green and growing, restored to its greatness.

But I think I’ll see it as a passenger, thank you. Because you just never know when someone will say, “Hey, let’s take Gough Street!”

And I’m just not going to go there.

Will Cutlip was born on the road, but parks his Honda in Brunswick.


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