A little over a year ago, while taking in the splendor that is Mugello, I was invited by my host to hop on a Ducati Monster — the 1200s Model — to canyon-carve the Dolomites. Like most of you would, I excitedly blurted “Yes” before “Would you like…” even rolled off my host’s tongue. There was just one catch: I’d have to ride bitch seat.

Three corners deep, I understood my wife’s every protest to straddling the postage stamp-sized seat of what passes for a passenger perch on most machines. (Not to mention the name — “bitch seat”.) There was no control within my grasp, so every dynamic move felt like a failing experiment with physics. There was simply no way I could enjoy this: being a passenger on a motorcycle sucks. Next time I’d wait until the question had been fully uttered. Lesson learned.

I was quizzed on this homework recently when an opportunity arose to experience the Ural Gear-Up Camp Wandawega Special Edition, at the camp’s home base in Elkhorn, WI. I paused to let things digest. The Ural — existing in the grayest of areas between ridiculous and amazing — is a strange beast. The product of a Soviet-shared, WWII Nazi design, it’s basically a beefed-up 1930s BMW R71 that has since added fuel injection, disc brakes and very little else. As a motorcycle, it’s a laughing stock — the 750cc boxer twin engine sputters out a measly 41 horsepower and the bike weighs almost 500 pounds — but a Ural isn’t just a motorcycle. Its a motorcycle with a sidecar.

Sliding my six-foot frame into the antiquated metallic pod mounted to the right hand side of the Ural, I was surprisingly comfortable. I had a wide padded seat, ample leg room, an angled backrest, a windshield and storage space in the floorboards to keep a camera at the ready. I could even carry on a conversation with the man in the saddle — hell, if I’d packed the right helmet, I could have enjoyed my morning coffee and smoked a cigar. This beats pillion any day of the week. There is an undeniably dignified civility to riding in a sidecar. It’s the motorcycling equivalent to being chauffeured in a Rolls Royce — albeit a malaise-era model that’s had its leather and wood stripped out to fund fuel and pay off the Russian mob. No wonder dogs love it so much.

Modern Classic Gear Suited to a Sidecar
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Suiting up in full knee-drag gear seemed like overkill — especially around the campfire — so we went with a modern classic approach.

Spidi Worker Wax H2Out Jacket
The waxed cotton jacket has been a mainstay for motorcycle riders since two-wheeled inception. Where the originals from Barbour and Belstaff still ooze that original cool, Spidi’s interpretation takes a modern approach. A tailored fit, linseed oil coated Egyptian cotton construction, EN1621-1 certified armor and removable waterproof and thermal liners combine to make this the ultimate iteration of a 200-year-old design. The best part is, the armor slides out in no time at all, making the Worker Wax H2Out a perfect transitional casual jacket. ($850)

Topo Designs Denim Work Pants
I aim to subscribe to the ATGATT (All the Gear, All the Time) philosophy whenever motorcycles are around. Sometimes my aim is little off. That being said, the double-layered, 12-ounce raw denim legs of the Topo Designs Denim Work Pants offered far more protection than my favorite Levi’s, all while nailing the Camp Wandawega aesthetic. ($149)

Wolverine Courtland 1000 Mile Boot
The Horween Chromexcel leather upper of a Wolverine 1000 Mile Boot is a thing of beauty. Buttery soft, yet tough as nails, they offer a supportive footbed and all-day comfort both in the saddle (and sidecar) and walking around town. Even after some punishing off-road miles, a quick wipe and shine is all it takes to bring them back to life. ($385)

Piloting a Ural, on the other hand, is not relaxing. Not at all. Every movement is engaging both mentally and physically. Two-wheeled beasts demand focus as well, but all behave the same way. Some are faster, louder, better than others, but they’re always predictable. Urals buck that convention. Crack the throttle, and the Siberian sled yaws to the right. Not unlike torque steer in an overpowered front-drive car, you’re immediately called into corrective action. This effect is mirrored as soon as you roll off the throttle and amplified under braking, feeling as if the ass end just broke loose. The whole ordeal is a workout, and that’s just to travel in a straight line. Cornering is a whole other story.

Where turning on a motorcycle involves push-steering to initiate a lean, corners with a sidecar rely on directing the front wheel. You manipulate the bars far more rigorously and turn them into the apex. That itself takes getting used to, but with an extra 200+ pounds hanging off your right side, there’s even more to consider. Left turns are a breeze — you can chuck the bike into a left bend much faster than you’d think — but hanging a right can get scary, fast. Commit too quickly or turn too abruptly, and that sidecar will seek unfindable balance, somewhere above your helmet. It will try to kill you.

The inherent danger to the enterprise creates a riding experience unlike anything else. Even the most powerful street-legal superbikes don’t emote the same adrenalized glee — they’re easy to ride fast, sure. But to master a Ural, you have to understand an art form — one that rewards as well as it punishes. The Ural is exhausting and exhilarating, and, riding around the roads and trails surrounding Camp Wandawega, this Siberian-built sled brings together old and new in raucous collision. It’s demanding, tricky, and — on sleepy, lakeside summer days — infinitely enthralling.