Two motorcyclists meet during a night out in Chicago on the 2024 Harley-Davidson Nightster Special.
Words by Steven Richards
Photography by Sandon Voelker
The bridge overhead shakes as an L-train speeds by, causing dirty water to fall onto the helmet of Shaun Guardado, who sits at a stoplight in downtown Chicago on a “Red Rock” 2024 Harley-Davidson Nightster Special. He calmly wipes clean his visor and, when the light turns green, takes off through the tendrils of rush-hour traffic on the Kennedy Expressway to arrive at Wild Wind Tattoo, where shop owner, Rich Marafioti, inks the first sharp lines of an extinguished but still smoking matchstick onto the rider’s forearm.
One mile north of the tattoo shop, Cait Bergeon parks her “Baja Orange” Nightster Special against the curb on West Fullerton Avenue, pulls off her helmet, and shakes loose her long, blonde, dreadlocked hair. Passersby stare as she walks into an old brick building that has a vintage “hardware” sign hanging from its façade, but inside is Logan Arcade, a bustling modern bar and video game arcade with over 70 blinking and ringing games, including the ten-player cult favorite, Killer Queen. Bergeon buys a soda from the bar, walks to the back room of the building, drops a dozen quarters into a pinball machine, and settles in for a few hours of flippers, bumpers, tilts, and jackpots.
How oddly alluring it is that these two motorcyclists, both on Nightster Specials, are in the same city and separated by only nine blocks but remain complete and utter strangers. It is not an uncommon scenario in the motorcycling community— meeting someone new at a motorcycle rally, or at a roadside diner, or at a crossroads at the edge of the world, only to find out that they live one town over— and sometimes all it takes to find a new lifelong friend is riding out into the dark, quiet cold of night.
“At night, the rest of the world falls asleep, and the roads open up, and suddenly you’re just out there, cruising and free,” Bergeon says. “I usually don’t have a plan— just going where the night takes me.” Her sentiment is shared by Guardado, who says, “Motorcycling is meditative, allowing you to be with yourself, to be present in the moment, but it’s amplified at night because there are not as many external stimuli, fewer people, and less distractions. It’s just you, the motorcycle, and the environment you’re riding in.”
When Guardado is wrapped with his tattoo appointment, he rides down back streets and through alleyways on his way toward “The Loop,” and after Bergeon runs out of quarters, she takes the highway toward beautiful Lake Shore Drive, but soon both riders find themselves under the flickering yellow lights of Lower Wacker Drive and arrive simultaneously at the same late-night spot: The Original Billy Goat Tavern.
At this underground burger saloon, made hilariously famous by Saturday Night Live’s “Cheezborger” skit featuring comedians Dan Akroyd, John Belushi, and Bill Murray, a motorcycle meet-cute unfolds at the old wooden bar as the two riders sit on their stools, snack on double cheeseburgers, sip on their Pepsis— no Coke! —and swap stories with the regulars in the “Wise Guy’s Corner.” They talk about long-ago motorcycle trips, unique details on their custom builds, and sweet memories from bike shows, and they laugh until the bar closes, then go their separate ways on their Nightster Specials.
Guardado says, “Even if you don’t know who is beneath that other helmet, you understand that you’re doing the same thing, even if you’re heading to different destinations. You get to share a short moment of adventure with someone you might not necessarily have anything else in common with, who you’ll likely never see again.”
Pack it: Capstone Sun Shield II H31 Modular Helmet
If you plan to ride from dusk until dawn, consider wearing the Capstone Sun Shield II H31 Modular Helmet, which has an integrated smoked sunshield behind its clear visor that easily retracts up after sunset and drops down before sunrise. The helmet’s lightweight polycarbonate composite shell features two intake vents and one exhaust vent and is DOT and ECE approved.
Eat. Sleep. Drink.
EAT
Al’s: In 1980, Chicago Magazine called out this shop for serving the “#1 Italian Beef Sandwich,” which holds true today.
Golden Apple Grill & Breakfast House: A 24-hour diner that offers delicious breakfast favorites no matter when you stop in.
Superdawg: A classic drive-in that serves Chicago-style hot dogs with mustard, relish, onions, hot peppers, and a dill pickle.
SLEEP
Chicago Athletic Association: High-end accommodations, a social games room with indoor bocce, and a rooftop bar overlooking Millennium Park.
The Drake: At the corner of Lake Shore Drive and the Magnificent Mile, America’s “first urban resort” is known for its grand rooms and opulent suites.
The Ohio House Motel: An affordable, city-center motel that is a short walk or a quick ride from some of the best shops and restaurants in Chicago.
DRINK
Jimmy Mack Bar: Known as “Bo’s” by locals, this divey, cash-only biker bar feels like it should be in downtown Sturgis, not six miles from O’Hare airport.
Logan Arcade: This former hardware store has dozens of new and classic arcade games and rotating taps of popular local beers.
The Original Billy Goat Tavern: Located on Lower Wacker Drive, the iconic, neon-lit “cheezborger” bar is a legendary late-night spot in the Second City.