Destination Wednesday: Favorite Fall Drives, With A Soundtrack

Fall is the best driving season of all. The views are spectacular, the air is crisp, the skies are that special shade of hard, brilliant blue, and you usually have the option of windows open or closed, not to mention top up or down.

‘Tis the season of corn shocks in the fields, the smell of burning leaves in the air, apples and pumpkins at roadside stands, and innumerable stories about great fall drives. For our take on the archetype, we’ve chosen to recommend a favorite vehicle (within reason) and soundtrack for each of our favorite fall drives.

Split Rock
Eerie yet beautiful, the eponymous lighthouse at Split Rock Lighthouse State Park, Minnesota.

The drives are listed from first – the earliest peak color – to last, so with no further ado, let’s synchronize our Spotify and go.

Lake Superior Circle Route/Cadillac CTS-V Wagon: The Circle Route circumnavigates the world’s largest freshwater lake while taking you from the U.S. to Canada and back again. The terrain varies from lighthouse-capped crags to sand dunes to white birches to near-mountains. All that terrain and distance demands a vehicle that can comfortably eat the miles. SUV-averse as we are, we gladly embrace the better thing – the station-wagon version of Cadillac’s rompy CTS-V. This particular model (which answers the question, “What would happen if I put a Corvette engine into a station wagon?”) is good as dead, but low-miled factory-certified used varieties are plentiful. As for music, see how many miles you can go on nothing more than Gordon Lightfoot’s “Wreck of the Edmund Fitzgerald.” Given a reasonable exceeding of the speed limit, we say … four.

New Hampshire State Highway 16/Subaru Outback: More people think of Vermont and fall colors, but we’re partial to NH 16, a winding line that spins out of Portsmouth past Mount Washington and almost into Canada before turning west and eventually south, and terminating at the University of Maine in Orono. NH 16 goes through some of the Northeast’s wildest country, a rugged mix of rocks, pines and glowing hardwoods. We’ll tackle it in the redesigned Subaru Outback; it’s not the best choice for the twisties, but you’re not allowed within 10 miles of Mount Washington without one, and you’ll so fit in when you stop for gas. Put some Phish through the speakers – Billy Breathes is our most-tolerated choice – and some Ben and Jerry’s in the cupholders and this section of the world will be yours.

Blue Ridge Mountains/Mazda Miata: Base yourself in Roanoke and do two out-and-backs: north and east on the Blue Ridge Parkway to Shenandoah National Park and Skyline Drive, and south and west on U.S. 19 to Asheville. Be prepared to go not fast; the parkways will be jammed with leaf-peepers, almost all in vehicles more unwieldy than our choice, the sweet, small, and sophisticated Mazda Miata. The Miata is the classic modern convertible sports car, and has been since we were little. It’s light, nimble, more than powerful enough, and never fails to make us smile when we get behind the wheel. With a soundtrack heavy on Doc Watson, the Carolina Chocolate Drops, and Old Crow Medicine Show, we’ll be more than willing to drive our Miata until the hills turn gold and steel-blue and the moon rises over the mountains.

Minnesota State Highway 95/ Wisconsin State Highway 35/Volkswagen GTI: Start north of the Twin Cities on Minnesota 95, in the cute-as-a-bug’s-ear town of Taylors Falls, follow the St. Croix River south on 95 until you reach the even-cuter town of Stillwater, then dart across the river, skirt the sprawl, and follow WI 35 south. Soon the St. Croix morphs into the Mississippi, the towns get smaller, and the bluffs and views get positively huge. Postcard town follows postcard town all the way down to Prairie du Chien and Wyalusing State Park. For this road, nothing beats a Volkswagen GTI. The Swiss Army Knife of sporty little things, the GTI is fast in the straights, professionally nimble in the curves, comfy under all circumstances, and just kooky enough – plaid seats! – to satisfy the hipster in all of us. Speaking of hipsters, we like Bon Iver (especially its eponymous album) for the Wisconsin phase of the trip and Jayhawks (the just-reissued Tomorrow The Green Grass will do) for the Minnesota part. But if you sub in some Replacements, we won’t argue.

Ozark loop/Chevrolet Camaro: Fall color eventually works its way south, and it’s never better in the south than in the Ozarks (or, as my daughter billed them alternately, the Aztecs and the Aardvarks). The problem is that there’s no good starting and ending point for a point-to-point trip; consequently, we recommend a Branson-based loop. Your feelings about Branson are semi-irrelevant, as you won’t be staying there long. Our favorite loop heads north and east out of Branson on Missouri 76 around Table Rock Lake. From there the loop goes (hang with us): on 76 through the Mark Twain National Forest to Missouri 125 south to Missouri 160 east to Missouri 95 north, then back to 76 to Missouri 181 to U.S. 60 to County Highway D to Missouri 14 to County T to Missouri 125 to County H to U.S. 160, and then U.S. 65 back to Branson. (It makes a lot more sense on a map.) You need some American iron to tackle these roads, ideally with a nav system. That eliminates the rebadged Australian Chevrolet SS but leaves the door wide open for the Chevrolet Camaro. The Cam comes in every flavor from chili-lime to Scotch bonnet, with a wide variety of drop-tops, and every model has heart, soul, and muscle. This drive demands  southern rock with a heart-of-America swirl, and we’re going dark-horse with The Mighty Jeremiahs, a semi-supergroup that features members of Wet Willie and the Kentucky Headhunters. Their stuff is hard to find, but you can easily drive into the sunset to the strains of “It’s Been A Good Day” … day after glorious fall day.

Photos from Wisconsin Department of Tourism, State of Arkansas, New Hampshire State Parks, and

Author: Kit Kiefer

As content engineer for Berkshire Hathaway Travel Protection, I have one of the world's great jobs. Not only do I get to write about travel, but I get to edit the work of fantastically talented contributors from around the world. Plus I get all the maple syrup I can drink.