The Road to Sturgis: Riding from Toronto to Michigan

The journey to the 84th Sturgis Motorcycle Rally is underway, and it’s already proving to be an adventure filled with laughs, unexpected detours, and the inevitable chaos that comes with a road trip of this scale. From Toronto to Michigan, the ByAppointmentOnly crew—Myles Cupitt (@tattookid13), Justin Steele (@steeleneedles), and Judy Cai (@jc_tattoos)—is hitting the road with their Harleys, a mobile tattoo van packed to the brim, and enough energy to fuel the miles ahead.

There’s a lot of excitement in the air, especially for Justin, who’s hyped about crossing into the U.S. for the first time. But before they even hit the border, there are a few hurdles—misplaced shoes, last-minute packing struggles, and, of course, figuring out how to strap everything down securely.

Rain, Roadblocks, and Laughter

The road from Toronto to Michigan isn’t just a straight shot—it’s a test of patience and endurance. Between gas stops and bathroom breaks (with an unfortunate frequency), the group faces torrential rain that soaks them to the bone. With every mile, there’s a new challenge, from avoiding semi-truck spray to dealing with wet boots and soggy clothes. And let’s not forget the endless snacks fueling their journey, with the van quickly becoming a treasure trove of chips and questionable convenience store purchases.

As they push through the rain and fatigue, spirits stay high with non-stop antics and plenty of roadside camaraderie. Whether it’s discussing their next gas station stop, dodging sketchy backroads, or dealing with unexpected power steering issues in the van, it’s all part of the adventure.

Crossing the Border

After hours of riding, the crew finally hits the Canadian-U.S. border, and tensions are high as they wait for Justin to get through customs. With jokes flying about fingerprints and cavity searches, they watch and wait—until, miraculously, he’s cleared. The relief is palpable, and it’s on to the next leg of the journey with the U.S. ahead and Sturgis getting closer by the mile.

Their first major stop? Motown Harley-Davidson in Taylor, Michigan. The shop offers them a warm welcome, and after picking up a few essentials (including the much-coveted Harley bell for good luck), they’re back on the road, now deep into the heartland of America.

Roadside Shenanigans

A road trip with this crew wouldn’t be complete without some hilarious moments—like discovering a cannabis store right next to a gas station (“devil’s lettuce, anyone?”) or marveling at the sheer abundance of cheap beer on American shelves. Then there’s the ever-present battle with road fatigue, with the team leaning into humor to push through the exhaustion.

By the time they roll into New Buffalo, Michigan, they’re ready for some well-deserved food and rest. Between wings, beer, and a little reflection on the day’s misadventures, it’s clear that despite the challenges, they wouldn’t trade the experience for anything. The mix of frustration and fun, camaraderie and chaos—that’s what makes a road trip to Sturgis truly unforgettable.

The Road Ahead

With day one in the books, the team has covered a lot of ground, but there’s still a long way to go. Sturgis awaits, and if the journey so far is any indication, the road ahead is bound to be filled with even more epic moments, unexpected detours, and plenty of stories to tell.

As they prep for the next leg of the trip, it’s clear that this isn’t just about getting to Sturgis—it’s about the experience of the open road, the friendships built along the way, and the shared love of motorcycles that fuels their journey.

Watch the entire adventure by checking out their YouTube channel and follow them on Instagram at @byappointmentonlytheshow. With more miles ahead and plenty of wild moments to come, this is one ride you won’t want to miss.

Follow the crew:

Myles Cupitt – @tattookid13

Justin Steele – @steeleneedles

Judy Cai – @jc_tattoos

Remember—no road trip is complete without a little chaos, a lot of laughter, and, of course, plenty of gas station snacks.