2018 Harley-Davidson Street Glide Special vs. Indian Chieftain Dark Horse

Bikes such as the Harley-Davidson Street Glide Special and Indian Chieftain Dark Horse account for most of the motorcycles purchased in this country every year. Yet, to me, they hardly make sense. They're heavy, low, and are meant to mosey along at a stately pace befitting their almost museumlike quality of being from another time. I know I'm in the minority, and in an effort to understand why, I decided to perform an experiment.

What if I were dropped halfway between the ­muddy banks of the Mississippi River and the shimmering shores of the Pacific Ocean, and told to make my way home? Would I understand those big bikes then? That became the mission: a roadracer, obsessed with horsepower and handling, astride baggers pointed across the heartland, in a mission to discover how and why ­American machines became what they are.

The lumbering persona of a low-slung, American V-twin is largely on purpose, with fuel injection, heavily engineered combustion chambers, and modern suspension under their skin. None of this is obvious. We don't see the passages for liquid to swirl around in the Street Glide's top end, or the oil jets cooling the bottom of the Chieftain's pistons. Forget emissions regulations; what we see is the Harley's burly, blacked-out muffler shooting back under a rakish saddlebag, and the Indian's chrome header dropping down at a contradictory angle from the overhead valves. Looks like vintage, tastes like vintage.

In reality, both Harley-Davidson and Indian have sprinkled technology from fender to fender. The list between the two is long: huge disc brakes with Bosch ABS, satellite navigation, LED lights, remote keys, and enough watts in the sound system to shake ripe fruit from a branch. Cruise control, color screens, and Bluetooth connectivity. And yes, those enormous engines. The Street Glide uses a four-valve, precision-cooled V-twin spread at 45 degrees to avoid blasphemy, displacing 107 cubic inches. A massive 111ci mill in the Indian requires a 49-degree V to keep the cylinders away from each other, while it uses a more conventional two-valve setup and the wind whistling past to keep cool.

It’s easy to dismiss the numbers, but 111 cubic inches is an astonishing 1,819cc. There are Honda sedans with less displacement. We got to this place of behemoth powerplants in our motorcycle culture because gasoline was low quality in the formative years of internal combustion and couldn’t be squeezed too aggressively. Low compression ratios meant there was never going to be much torque on hand unless the engines were made bigger. At one point, the U.S. Postal Service required that motorcycle engines used for delivery be no less than one liter (61 cubic inches). The engines got bigger, which, in turn, led to reinforced frames. The machines grew.

These engines are huge, and so are the rest of the bikes—even for me at 6-foot-2 and nearly 200 pounds. The fat grips feel like they were made for Andre the Giant, and are combined with size-16 floorboards and wide fuel tanks. That adds up to the Street Glide ­Special and Chieftain Dark Horse weighing well north of 800 pounds each. The Harley’s Milwaukee-Eight engine is liquid cooled, and the Indian has an ­electronically ­adjustable windscreen and power locks on the ­saddlebags. Those things—and everything else that has made the bikes bigger—all add weight.

In the early days of motorcycling, an Indian’s exhaust exited down because side valves were the way to do it—Briggs & Strattons strapped to bicycles in modern terms. When everyone demanded more power, the easiest thing to do was add another cylinder to the existing crankshaft and, in order to keep those already huge bicycles narrow, it made sense to splay the cylinders into a V-twin. As clattery and unrefined as they were, those turn-of-the-century cylinders firing in pulses planted an acoustic seed. The roots of the obsession we have with V-twins go back to the beginning of the innovation and evolution of motorcycles.

We brought this obsession and latest evolution of the American V-twin to Medicine Bow, Wyoming, to ride west across the plains, climbing the gentle eastern slope of the Continental Divide. It was a tall sky that made me feel small. Speed limits at or approaching 80 mph meant we kicked the steeds into a canter and made great time. I spent hours on the Street Glide gazing wistfully through a blur of helmet buffeting as the Chieftain’s power windshield rose up from the batwing fairing. That must be nice, I thought. In both cases, with the cruise set, the bikes were as stable as locomotives comfortable, so long as the La-Z-Boy riding position suits you. If you slouch for better wind protection, like I did, the wide seats won’t save your spine.

The thunder of a big twin across the plains has a ­timeless ring. I thought about those pushrods flying around inside the engine and how the experience wouldn’t be the same without them. For me, being connected to the machine is a special piece of enjoying a motorcycle ride. Everyone’s favorite bike has some quality that another does not. Some bikes want to lean over, some are easy to stall. Others seem excitable, like they could take off in any direction. And there’s a mechanical reason for all of it.

We took to two-lane for the better part of Utah, ­trickling south from the southwest corner of Wyoming to Zion National Park and the gateway to Las Vegas. Frigid rain passing through an 11,000-foot pass tested the fairings, and I came to know a truth that so many have learned before: Weather protection is proportional to miles per hour. We warmed up our pride and our fingers swimming in a geothermal crater outside Provo, Utah.

The practical use of the bikes became pretty clear. The Harley’s saddlebags felt sturdier, and the latch is a work of art. On the other hand, the Indian’s 7-inch touchscreen infotainment system made Milwaukee’s interface feel a full generation behind. It’s a complete rethink of what that system should be on a motorcycle, not simply an evolution of what’s always been there.

Harley’s Street Glide Special can be traced ­pretty ­directly back to the baby boom, at least in basic ­architecture. Its swagger, in the right light, still glints with midcentury charm. The streak of nostalgia is even brighter on the Chieftain, mainly because of that engine—the rounded heads with comb-over fins hearken back to postwar Indians with the year “1901” stamped brazenly on the case. It is both the centerpiece of the bike and a resurrection of the machines that tattooed the brand into American lore.

Las Vegas has a similar feel—historic and sentimental but laced with technology. As capable as these two machines are at hauling camping gear and gobbling up miles, the experience of grumbling down the Vegas Strip with a whiff of Rat Pack debonair and modern tech was too perfect. I was loving it. The Harley was in its element, glittery bodywork pulled taut over a furrowed brow. Indian’s Dark Horse matte paint soaked up the neon of Vegas, the fairing sweeping back like the front of an art-deco train at full speed. I would have been more comfortable on an adventure bike, but I would have felt like a dweeb. Instead, I felt at home.

Getting across the country isn’t hard anymore, but these bikes still include DNA from an era when it was more than a four-day ride or a five-hour flight. The Indian did it all more gracefully. As gorgeous as that 111 engine is to look at, I didn’t expect the Chieftain to be so impressive, but I was consistently amazed at how well it worked. The Harley is still better looking—it is pure and classic, and I wouldn’t change a line on it. I realized that part of the reason American V-twins feel old-fashioned is that they are solving an old problem: to simply get down the roads of this vast nation. That’s still a good problem to solve.

The machines we love are a product of the environments we strive to conquer. The American V-twin simply wouldn’t have come to be without America itself. For the ingenuity, bravery, and will to persevere, yes—but also for the land on its own. The voids in civilization and the need to ride across them.

That is the attitude that conquered the West, which is why we always hear that a journey can be for journey’s sake. The meaning of the destination is defined by the path taken to get there, not the goal of having arrived. So it is with the American West, and the American bagger—the ocean of California wouldn’t sparkle as ­brilliantly if the jagged peaks and vast prairie didn’t require such fortitude to overcome.