In the Rearview Mirror: My all-time favorite roads

July 13, 2026

“My Next One” is what a lot of car collectors will respond when asked, “What’s your favorite car?”

The same is true of roads. There’s nothing wrong with the highways and byways that you’re used to. The ones you know so well you could probably drive blindfolded. The kind you tell your friends about when the subject turns to “best roads ever.” The kind that pop to mind when you daydream.

But we all love something new to try. That, of course, is the impulse behind our annual Road of the Year award and special issue of Hagerty Drivers Club magazine, which is always my favorite. Hats off to the Hagerty Media team for finding a route that I and most of the motoring public have never heard about or driven before.

Pennsylvania Route 144, in fact, is so obscure that I had to look it up. Here’s what I found: “Pennsylvania Route 144 (PA 144) is a 109-mile (175 km) state highway in central Pennsylvania… renowned for the ‘High Plateau Scenic Byway’ section between Snow Shoe and Renovo, which offers remote, mountainous scenery through the Sproul State Forest. Terrain: Features sharp, winding turns, steep elevation changes, and switchbacks, particularly descending into the Susquehanna River Valley near Renovo.” Sounds good to me. I’ve added it to my bucket list.

The great thing about driving-road bucket lists is that every driver has one. Stories like the one in this issue spur people to share their lists as well.

Here are three of my favorite roads, and a few I hope to visit someday.

1) First for me is M-22 in the pinkie of Michigan. I’ve mentioned it before, but it bears repeating because it’s so darned enjoyable—the most pleasant road I know of in one of the prettiest places on the planet. The road runs for dozens of miles along Lake Michigan, through the Sleeping Bear Dunes National Lakeshore, and past Little Glen Lake, once named (along with its brother, Big Glen Lake) by National Geographic as one of the most beautiful in the world. I grew up and still live about 30 miles from this delightful region, and it never loses its hold on me. The car I most often drive there is the restored 1967 Porsche 911 S that I rebuilt from scraps with my dad. For one hot, brief summer, he drove a modified Ford pickup truck atop those dunes, giving tourists a thrill. After years of searching, we found one of those pickups and restored it. We use it in local parades.

2) Nicknamed “Rossi’s Driveway” after Carlo Rossi, the famous jug wine producer, California State Route 229 is a 9-mile roller coaster (up and down, up and down, rinse and repeat) of a road in Central California. The scenery is a lovely mix of mountains, rolling hills, and meadows, but it’s a challenging drive that requires your attention and respect—especially a stretch on the southern portion of the route where the lanes are narrow and (when I was there) largely unmarked. Keep your eyes on the road, not the views.

3) California State Route 1 in Big Sur is one you’ve probably heard friends gush over. Sometimes praise like that can make your eyes glaze over and you think, “Nah, everyone’s done that.” Well, in this case, there’s a reason for that: It is spectacular. The waves, the water, the cliffs—this is one endlessly hyped route that you truly shouldn’t miss. It’s a destination drive that will become one of your favorites.

OK, now for my bucket list. Before I depart this vale, among the roads I want the pleasure to have known are Route 66 (everyone has to once, right?), the Targa Florio in Sicily, Canada’s Alcan Highway, Japan’s iconic Mount Haruna Pass, and Stelvio Pass in Switzerland.

Have additional choices for me? Comment below.