Road trip! Our favorite driving adventures, both foreign and domestic

Davin Reckow behind the wheel of the Hagerty's Swap to Street Model T

Road trips. We’ve all taken them, and it seems the longer the drive, the more memorable the trip. Of course, if you’re jammed into a car with six kids, a dog, and no air conditioning, the word “memorable” doesn’t necessarily mean “awesome.”

But we’re looking on the bright side. As we head into the unofficial last week of summer, we asked members of Hagerty’s Media Team to consider, “What’s the best road trip you’ve ever taken?” Here are their picks:

Ben Woodworth, Colorado to Oregon and California—I’ve had so many great road trips! It’s hard to pick just one, but I think I’ll go with a road trip I took with a friend in the spring of 2009. The ski season had just ended in Colorado and we were jonesing for some more shred time. So we packed up my 1991 Honda Civic and drove from Dillon to Mt. Hood, Oregon, to get our fix. At every gas station (mostly Flying J truck stops) we took out a soccer ball and juggled in the parking lot for 15–20 minutes before continuing on our way.

My gas gauge didn’t work very well, but I knew I could get about 350 miles on a tank full. That estimate worked well until we had to go over a big mountain pass somewhere in Idaho. We were about halfway down the other side, with the trip odometer at about 250 miles, when my Honda started struggling. I turned off the car and coasted 5–6 miles down the rest of the pass, hoping that there would be a gas station at the bottom. After the highway flattened out I was able to start the Civic and get another mile or two out of her before slowly drifting off an exit ramp and into a gas station.

We ended up staying in Mt. Hood for a day. The weather was terrible, so we headed south to Redding, Calif., to meet some friends. After that we drove to Crowley Lake, Calif. (near Mammoth Lakes), and wake-surfed with another friend for four days, then headed back to Summit County, Colo.

We covered about 2,900 miles in that week, and although our initial plan was to go to Mt. Hood and back, it turned into the best kind of road trip—the kind where you go wherever you want, whenever you want. I’d do it again tomorrow. Same friend. Same car.

Ben Woodworth with friends in Crowley Lake, CA
Ben Woodworth
Ben Woodworth with friends in Crowley Lake, CA

Carolyn Greenman, Michigan to East Coast—The best road trip I’ve ever taken was just a couple of weeks ago. My husband and I had never taken a long road trip, and we planned to tent camp our way east from Michigan, bringing only what was absolutely necessary. I had never been out of the country before, but on a hot and humid Friday afternoon, we set off for Canada—and, eventually, the eastern U.S.—in a rented Nissan Rogue with 800 miles to its name.

We drove to the Finger Lakes region of New York to taste the nectar of the gods, cultivated from the vineyards strewn about the area. We roamed through the Green Mountains of Vermont, where we ate delicious cheese and hiked to breathtaking vistas. We wound our way through Maine and landed in Acadia National Park (a suggestion from the “Barn Find Hunter” himself, Tom Cotter), and learned of famous French explorer Antoine de la Mothe Cadillac, founder of Detroit and namesake of Cadillac Mountain.

From Maine, we set course for Halifax, Nova Scotia, a place we heard had sights as wondrous as Scotland. The voyage was roughly nine hours long, and the Rogue served us well, not only for transportation but as a container for all the treasures we gathered and a comfortable place to nap as needed. On a bright Saturday morning, we parked in downtown Halifax and walked around the city. There was a parade going on, so we watched for a bit—just long enough to get a glimpse of Prime Minister Justin Trudeau and his family strolling past.

We retired to our campsite and enjoyed the last night of our trip, staring out at the Atlantic Ocean and smiling with satisfaction, then left for home the next day. We rolled into our driveway with 4,200 miles on the odometer, and no flat tires, accidents, tickets, or scratches. Wonder what our next road trip will be?

Cody Wilson, Oregon to Montana—My favorite road trip was with my dad in his fully restored ’66 Sunbeam Tiger. He restored it over the course of 14 years. We drove it from Billings, Montana, to from Portland, Oregon, which is about a 17-hour drive.

Evelyn Demirjian, California’s Pacific Coast Highway—The only real road trip I’ve taken was down the coast of California with my dad. We went to tour colleges, but he surprised me by renting a white 2010 Ford Mustang convertible. We drove with the top down from San Francisco to San Diego, stopping at each college along the way. Considering that we are from Chicago, the 60-degree weather felt amazing to us, so we were cruising in t-shirts the whole time. But every time we stopped to eat, we would get weird looks from all the Californians in North Face coats and UGG boots. I definitely need to go back someday; those In-n-Out burgers are delicious.

Hagerty's Swap to Street Truck and Model T
Yoav Gilad
Hagerty's Swap to Street Truck and Model T

Jeff Peek, Michigan to Texas—I’ve thoroughly enjoyed the many spring-break road trips I’ve taken from Michigan to Florida, first as a college student and later as a dad, but I still consider this the “best” road trip I’ve taken … probably because the older I get, the more magical my childhood seems.

In the summer of 1976, my parents decided it would be a great idea to load themselves and five kids into an orange-and-yellow Volkswagen bus and visit some relatives in Paris. No, not that Paris—driving across the Atlantic Ocean would have been quite a trick—but Paris, Texas. It didn’t matter. When you’re 14 years old and have never been out of your home state, you don’t care if you see the Eiffel Tower, Sears Tower, or Devils Tower. Whatever, let’s get outta here.

I have so many happy memories of that 2,500-mile adventure, which included crossing the Mississippi River, seeing the Gateway Arch in St. Louis, camping in Arkansas, buying Dallas Cowboys and Texas Rangers pennants from a blue-roofed roadside Stuckey’s, spending a day at Six Flags Over Texas, playing the road-sign ABC game (practically ad nauseam), and rediscovering just how much I enjoy hanging with my family. I’d take that trip again in a heartbeat.

Joe DeMatio, Michigan to New York and Boston—In July 1990, when the first-generation Mazda Miata was still a very rare and special thing, I had just started working for Automobile Magazine and was still pinching myself that I had access to brand-new test cars. This car—blue over black, with manual transmission, of course—wasn’t just any car, but the hottest car of the year, and it was all mine for 11 days. I drove from Ann Arbor (Mich.) to New York City on a Friday, listening to Sinead O’Connor’s breakthrough album, “I Do Not Want What I Haven’t Got,” repeatedly on the in-dash CD player. I gave the Miata to a colleague from our New York office for the weekend while I visited friends and danced at Roxy, the famous Chelsea club. By Sunday afternoon I was back in the Miata and heading north to Boston, where I had a week of computer training in a suburban office park. Each and every night I’d drive down to Boston and cruise around, top down, thinking I was something. Madonna’s “Vogue” was playing nonstop everywhere I went. On Friday afternoon, I headed south to Washington, D.C., where I met up with my friend Charley for the weekend for more top-down profiling. I was 24, it was high summer, and I thought life was pretty grand. And it was.

Jonathan Stein, Germany to France—The best road trip I ever took was from Stuttgart, Germany, to Mulhouse, France, in 1989. I drove a Mercedes-Benz AMG SL60, which was the current SL with the V-8 punched out to six liters. On the Autobahn I got the car up to about 135 mph on two occasions (which is legal, by the way) before I had to back off due to traffic. I hated my cheap “plastic” hotel, and after one night (and after I had visited the Schlumpf Collection—mostly Bugattis) I got into the car and headed west along the wine route. I found this spectacular medieval town in Alsace called Ribeauville’. The streets were so narrow that I could barely squeeze the wide SL between parked cars and stone walls. A room in a 300-year-old inn with crooked floors and a restaurant with a fantastic traditional menu made this trip one for the ages. It was the best solo road trip I’ve ever taken. Great car, great scenery, wonderful town, and wonderful traditional food—Choucroute garnie—washed down with a half bottle of the local Gewurztraminer.

Matt Lewis, Michigan to Nevada/California to Michigan—It’s probably a tie: driving Hagerty’s “Swap to Street” truck from Traverse City, Mich., to Las Vegas on the Driven Dirty Tour for SEMA and driving a ’65 Mustang (for our next employee restoration project) from California to Michigan. In both instances, Davin Reckow and I were largely considered idiots for driving an “unknown” old car thousands of miles without a backup plan. But we took it easy and made it just fine both times. We handled every hurdle (including a fuel tank problem on the truck and generator failure on the Mustang) by keeping our cool and finding a solution. (Davin Reckow adds: “Ditto. But I’d also include driving a Model T cross country, all on backroads, and bringing our ’66 Chevelle home from Albany, N.Y.”)

Nick Gravlin, Michigan to Idaho—When I was in elementary school my dad planned a massive cross-country road trip to visit my aunt and uncle in Idaho. We made the trip in our family’s 1994 Pontiac Trans Sport van, which was quite cramped with five passengers and luggage. We stopped at most of the historical sites along the way including (in no particular order):

  • Mount Rushmore
  • Deadwood
  • Yellow Stone National Park
  • Devils Tower
  • Little Bighorn Nat’l Battlefield Monument
  • Wall Drug Store
  • The Corn Palace
  • Golden Spike Nat'l Historic Site at Promontory

While I don’t fully remember all of the details of those locations, the thing I remember most was Bop-It. That toy was just becoming the “new big thing,” and our cousins gave us one to play with on the return trip to Michigan. Looking back, I can only imagine what my parents went through as my brothers and I played with that thing for hours in the back seat. I’m sure they’ll never forget the phrases Bop-it, Twist-it, and Pull-it.

Nick Gravlin with his family in front of Mount Rushmore
Courtesy of Nick Gravlin
Nick Gravlin with his family in front of Mount Rushmore